105-55-5

Basic information

• Product Name: N,N'-Diethylthiourea
• Synonyms: 1,3-diethyl-2-thio-ure;1,3-diethyl-2-thiourea[qr];1,3-diethyl-2-thiouree;1,3-diethylthiourea[qr];n,n’-diethylthiocarbamide[qr];n,n’-diethyl-thioure;n,n’-diethylthiouree;N,N'-Diethylthiourea (sym)
• CAS NO: 105-55-5
• Molecular Formula: C₅H₁₂N₂S
• Molecular Weight: 132.23
• EINECS: 203-308-5
• Product Categories: Industrial/Fine Chemicals;Organic Building Blocks;Sulfur Compounds;Thioureas
• Mol File: 105-55-5.mol
• Article Data: 13

Chemical Properties

• Melting Point: 76-78 °C(lit.)
• Boiling Point: 245°C (estimate)
• Flash Point: 186 °C
• Appearance: /solid
• Density: 1,12 g/cm3
• Vapor Pressure: 0.001Pa at 25℃
• Refractive Index: 1.5300 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: 42g/l
• PKA: 14.47±0.70(Predicted)
• Water Solubility: 38 g/L (20 ºC)
• Stability: Stable. May be air sensitive. Incompatible with strong oxidizing agents.
• BRN: 773905
• CAS DataBase Reference: N,N'-Diethylthiourea(CAS DataBase Reference)
• NIST Chemistry Reference: N,N'-Diethylthiourea(105-55-5)
• EPA Substance Registry System: N,N'-Diethylthiourea(105-55-5)

Safety Data

• Hazard Codes: Xn,T
• Statements: 22-40-45-20/21/22
• Safety Statements: 45-36/37-53-24/25
• WGK Germany: 2
• RTECS: YS9800000
• TSCA: Yes
• Hazardous Substances Data: 105-55-5(Hazardous Substances Data)

Usage

Description

Diethylthiourea, a thiourea derivative, is used mainly as a rubber chemical, particularly in solid neoprene products.

Chemical Properties

white to buff-coloured solid

Uses

Different sources of media describe the Uses of 105-55-5 differently. You can refer to the following data:
1. N,N′-Diethylthiourea can be used as a reactant to prepare:3,5-Diethyltetrahydro-4-thioxo-1,3,5-triazine-1(2H)-propanoic acid by condensation reaction with formaldehyde and β-alanine.Methyl 3-ethyl-2-(ethylimino)-3,4-dihydro-4-oxo-2H-1,3-thiazine-6-carboxylate by one-pot reaction with dimethyl acetylenedicarboxylate in the presence of triphenylphosphine catalyst. 2-(Ethylimino)-3-ethyl-thiazolidin-4-one by cyclization reaction with 2-chloroacetic acid. 3-Ethyl-2-(ethylimino)-4-oxo-5-thiazolidineacetamide by condensation reaction with maleimides via Michael-type reaction.
2. Diethyl thiourea is the inhibitor of corrosion in metal pick/ing solutions; accelerator for mercaptan-modified chloroprene rubber; antidegradant for natural, nitrile-butadiene, styrene-butadiene, and chloroprene rubbers

Definition

ChEBI: Thiourea in which each nitogen carries an ethyl substituent.

General Description

Buff solid or white powder.

Air & Water Reactions

N,N'-Diethylthiourea may be sensitive to exposure to air. . Slightly soluble in water.

Reactivity Profile

N,N'-Diethylthiourea is an amide. Amides/imides react with azo and diazo compounds to generate toxic gases. Flammable gases are formed by the reaction of organic amides/imides with strong reducing agents. Amides are very weak bases (weaker than water). Imides are less basic yet and in fact react with strong bases to form salts. That is, they can react as acids. Mixing amides with dehydrating agents such as P2O5 or SOCl2 generates the corresponding nitrile. The combustion of these compounds generates mixed oxides of nitrogen (NOx).

Health Hazard

ACUTE/CHRONIC HAZARDS: When heated to decomposition N,N'-Diethylthiourea emits toxic fumes.

Fire Hazard

Flash point data are not available for N,N'-Diethylthiourea, but N,N'-Diethylthiourea is probably combustible.

Flammability and Explosibility

Nonflammable

Contact allergens

Diethylthiourea, a thiourea derivative, is used mainly as a rubber chemical, particularly in solid neoprene products.

Safety Profile

Poison by ingestion. Moderately toxic by intraperitoneal route. Questionable carcinogen with experimental carcinogenic data. Mutation data reported. When heated to decomposition it emits very toxic fumes of NOx and SOx

Purification Methods

Crystallise it from *benzene. [Beilstein 4 H 118, 4 I 355, 4 II 610, 4 III 220, 4 IV 375.]

Synthetic route

Ethyl isothiocyanate (542-85-8) → N,N'-diethylthiourea (105-55-5)

Conditions	Yield
With water; triethylamine In 1,4-dioxane at 20℃; for 0.166667h;	99%
In pyridine; water at 60℃; for 48h; Condensation;	74%
With hydrogen sulfide

carbon disulfide (75-15-0) + ethylamine (75-04-7) → N,N'-diethylthiourea (105-55-5)

Conditions	Yield
In water at 20℃; for 0.166667h; Green chemistry;	99%
In water at 20℃; for 0.166667h; Green chemistry;	99%

ethylamine (75-04-7) + thiourea (17356-08-0) → N,N'-diethylthiourea (105-55-5)

Conditions	Yield
With PEG-400 In water for 0.00833333h; microwave irradiation;	96%

ureidoacetylaminoethanoic acid (17303-54-7) + 4,5-dihydroxy-1,3-diethyl-4,5-diphenylimidazolidine-2-thione (924851-22-9) + isopropyl alcohol (67-63-0) → 1,3-diethyl-5,5-diphenyl-2-thioxoimidazolidin-4-one (1350618-34-6) + isopropyl [2-(4,6-diethyl-2-oxo-3a,6a-diphenyl-5-thioxooctahydroimidazo[4,5-d]imidazol-1-yl)-1-oxoethylamino]acetate (1350618-33-5) + benzil (134-81-6) + N,N'-diethylthiourea (105-55-5)

Conditions	Yield
With hydrogenchloride; water Reflux;	A n/a B 77% C n/a D n/a

Ethyl isothiocyanate (542-85-8) + N-Phenylhydroxylamine (100-65-2) → 1-ethyl-3-phenylthiourea (2741-06-2) + N,N'-diethylthiourea (105-55-5)

Conditions	Yield
Stage #1: Ethyl isothiocyanate; N-Phenylhydroxylamine With magnesium oxide In acetone at 20℃; for 0.166667h; Stage #2: for 0.0666667h; Microwave irradiation; neat (no solvent);	A 76% B 12%

methanol (67-56-1) + N-carbamoylglycine (462-60-2) + 4,5-dihydroxy-1,3-diethyl-4,5-diphenylimidazolidine-2-thione (924851-22-9) → methyl (4,6-diethyl-2-oxo-3a,6a-diphenyl-5-thioxooctahydroimidazo[4,5-d]imidazol-1-yl)acetate (1350618-24-4) + benzil (134-81-6) + N,N'-diethylthiourea (105-55-5)

Conditions	Yield
With hydrogenchloride; water Reflux;	A 73% B n/a C n/a

N-Methylhydroxylamine (593-77-1) + Ethyl isothiocyanate (542-85-8) → 3-ethyl-1-methylthiourea (10220-04-9) + N,N'-diethylthiourea (105-55-5)

Conditions	Yield
Stage #1: N-Methylhydroxylamine; Ethyl isothiocyanate With magnesium oxide In acetone at 20℃; for 0.166667h; Stage #2: for 0.0583333h; Microwave irradiation; neat (no solvent);	A 71% B 13%

N-carbamoylglycine (462-60-2) + 4,5-dihydroxy-1,3-diethyl-4,5-diphenylimidazolidine-2-thione (924851-22-9) + isopropyl alcohol (67-63-0) → 2,4-imidazolidinedione (461-72-3) + 1,3-diethyl-5,5-diphenyl-2-thioxoimidazolidin-4-one (1350618-34-6) + isopropyl (4,6-diethyl-2-oxo-3a,6a-diphenyl-5-thioxooctahydroimidazo[4,5-d]imidazol-1-yl)acetate (1350618-30-2) + benzil (134-81-6) + N,N'-diethylthiourea (105-55-5)

Conditions	Yield
With hydrogenchloride; water Reflux;	A n/a B n/a C 69% D n/a E n/a

grateloupine (2609-10-1) + 4,5-dihydroxy-1,3-diethyl-4,5-diphenylimidazolidine-2-thione (924851-22-9) + isopropyl alcohol (67-63-0) → 1,3-diethyl-5,5-diphenyl-2-thioxoimidazolidin-4-one (1350618-34-6) + isopropyl 4-(4,6-diethyl-2-oxo-3a,6a-diphenyl-5-thioxooctahydroimidazo[4,5-d]imidazol-1-yl)butanoate (1350618-32-4) + benzil (134-81-6) + N,N'-diethylthiourea (105-55-5)

Conditions	Yield
With hydrogenchloride; water Reflux;	A n/a B 67% C n/a D n/a

N-carbamoyl-β-alanine (462-88-4) + 4,5-dihydroxy-1,3-diethyl-4,5-diphenylimidazolidine-2-thione (924851-22-9) + isopropyl alcohol (67-63-0) → 1,3-diethyl-5,5-diphenyl-2-thioxoimidazolidin-4-one (1350618-34-6) + isopropyl 3-(4,6-diethyl-2-oxo-3a,6a-diphenyl-5-thioxooctahydroimidazo[4,5-d]imidazol-1-yl)propanoate (1350618-31-3) + benzil (134-81-6) + N,N'-diethylthiourea (105-55-5)

Conditions	Yield
With hydrogenchloride; water Reflux;	A n/a B 66% C n/a D n/a

methanol (67-56-1) + N-carbamoyl-β-alanine (462-88-4) + 4,5-dihydroxy-1,3-diethyl-4,5-diphenylimidazolidine-2-thione (924851-22-9) → methyl 3-(4,6-diethyl-2-oxo-3a,6a-diphenyl-5-thioxooctahydroimidazo[4,5-d]imidazol-1-yl)propanoate (1350618-25-5) + benzil (134-81-6) + N,N'-diethylthiourea (105-55-5)

Conditions	Yield
With hydrogenchloride; water Reflux;	A 57% B n/a C n/a

N-carbamoylglycine (462-60-2) + 4,5-dihydroxy-1,3-diethyl-4,5-diphenylimidazolidine-2-thione (924851-22-9) + isopropyl alcohol (67-63-0) → 1,3-diethyl-5,5-diphenyl-2-thioxoimidazolidin-4-one (1350618-34-6) + (4,6-dimethyl-2-oxo-3a,6a-diphenyl-5-thioxooctahydroimidazo[4,5-d]imidazol-1-yl)acetic acid (1350618-18-6) + isopropyl (4,6-dimethyl-2-oxo-3a,6a-diphenyl-5-thioxooctahydroimidazo[4,5-d]imidazol-1-yl)acetate (1350618-26-6) + benzil (134-81-6) + N,N'-diethylthiourea (105-55-5)

Conditions	Yield
With hydrogenchloride; water for 1h; Reflux;	A n/a B 18% C n/a D n/a E n/a

Ethyl isothiocyanate (542-85-8) + ethylamine (75-04-7) → N,N'-diethylthiourea (105-55-5)

ethyl-thiocarbamic acid ; compound with ethylamine (64221-18-7) → N,N'-diethylthiourea (105-55-5)

Conditions	Yield
In ethanol Heating;

ethyl-dithiocarbamidacidic ethylamine → N,N'-diethylthiourea (105-55-5)

Conditions	Yield
With ethanol at 110 - 120℃; im geschlossenen Rohr;

mercury salt of/the/ N-ethyl-dithiocarbamic acid → N,N'-diethylthiourea (105-55-5)

Conditions	Yield
at 160 - 165℃;

N-ethyl O-ethyl thiocarbamate (998-98-1) + ethylamine (75-04-7) → N,N'-diethylthiourea (105-55-5)

Conditions	Yield
With sodium hydroxide In water for 0.5h; Heating;

ethylamine (75-04-7) + S-ethyl O-phenyl dithiocarbonate (116849-51-5) → N,N'-diethylthiourea (105-55-5)

Conditions	Yield
In acetone for 3h;

(3-chloropropyl)triethoxysilane (5089-70-3) + N,N'-diethylthiourea (105-55-5) → N,N'-diethyl-N,N'-bis(3-(triethoxysilyl)propyl)thiourea

Conditions	Yield
Stage #1: (3-chloropropyl)triethoxysilane With sodium hydroxide In toluene at 50℃; for 0.5h; Inert atmosphere; Stage #2: N,N'-diethylthiourea In toluene at 110℃; for 5h; Inert atmosphere;	97.8%

C6H9N3O3 (146000-76-2) + N,N'-diethylthiourea (105-55-5) → C16H26N8O5S

Conditions	Yield
In methanol at 25℃; for 0.5h; Cycloaddition;	97%

3,4-diphenyl-1,2,5-thiadiazole-1,1-dioxide (3775-15-3) + N,N'-diethylthiourea (105-55-5) → C19H22N4O2S2

Conditions	Yield
In dimethyl sulfoxide at 20℃; for 24h;	95%

methyl 2-[2-(anilinocarbonyl)-1-diazenyl]-1-cyclooctene-1-carboxylate + N,N'-diethylthiourea (105-55-5) → 2-[3-ethyl-2-(ethylimino)-4-oxo-1-thia-3-azaspiro[4.7]dodec-6-ylidene]-1-hydrazinecarboxamide

Conditions	Yield
In methanol at 20℃;	94%

formaldehyd (50-00-0) + glycine (56-40-6) + N,N'-diethylthiourea (105-55-5) → 2-(3,5-diethyl-4-thioxo-1,3,5-triazinan-1-yl)acetic acid

Conditions	Yield
In water at 20℃;	93%

Cyclohexyl isocyanide (931-53-3) + Ethyl oxalyl chloride (4755-77-5) + N,N'-diethylthiourea (105-55-5) → 6-(cyclohexylamino)-1,3-diethyl-6-hydroxyl-2-thioxotetrahydropyrimidine-4,5-dione

Conditions	Yield
With water In acetonitrile at 20℃; for 24h; Nef Reaction;	92%

N,N'-diethylthiourea (105-55-5) + methyl iodide (74-88-4) → S-methyl-N,N'-diethylisothiouronium hydriodide (32274-24-1)

Conditions	Yield
In methanol at 80℃; for 2h;	91%
With ethanol
With isopropyl alcohol

formaldehyd (50-00-0) + N,N'-diethylthiourea (105-55-5) + 3-amino propanoic acid (107-95-9) → 3-(3,5-diethyl-4-thioxo-1,3,5-triazinan-1-yl)-propanoic acid

Conditions	Yield
In water at 20℃;	90.9%

N,N'-diethylthiourea (105-55-5) → (ethylamino)(ethylimino)-methanesulfonic acid (117766-00-4)

Conditions	Yield
With sodium molybdate; dihydrogen peroxide In water a.) 0-10 deg C, 1 h, b.) RT, 20 h;	90%

dimethyl acetylenedicarboxylate (762-42-5) + N,N'-diethylthiourea (105-55-5) → methyl 3-ethyl-2-(ethylimino)-3,4-dihydro-4-oxo-2H-1,3-thiazine-6-carboxylate (669716-94-3)

Conditions	Yield
With triphenylphosphine In water at 50℃;	90%

N,N'-diethylthiourea (105-55-5) + silver(I) iodide → tris(N,N'-diethylthiourea-S)iodosilver(I) (207342-53-8)

Conditions	Yield
In acetonitrile AgI and ligand (molar ratio 1:3) mixed with MeCN; heated to boiling; cooled to room temp.; crystd. by seeding a small amt. of mechanochemically generate title compd.; crystals collected; washed with ice cold MeCN; elem. anal.;	89%
In acetonitrile warming AgI with 3 equiv. of ligand for 4 h; filtration, crystn. on slow evapn.;
In N,N-dimethyl-formamide AgCl and ligand (molar ratio 1:3) lightly ground to form homogeneous mixt.; DMF (1-2 drops) added; ground for a few min; dried; detd. by IR spectra;

N1-phenyl-2-(1-cyclohexenyl)-1-diazene-1-carboxylate + N,N'-diethylthiourea (105-55-5) → 2-[3-ethyl-2-(ethylimino)-2,3a,5,6,7,7a-hexahydro-1,3-benzothiazol-3a(4H)-yl]-N-phenylhydrazinecarboxamide

Conditions	Yield
In methanol at 20℃;	88%

Glyoxilic acid (298-12-4) + N,N'-diethylthiourea (105-55-5) → C7H12N2O2S (1239420-46-2)

Conditions	Yield
In toluene at 80℃; for 4h; Inert atmosphere;	87%

tert-butylisonitrile (119072-55-8, 7188-38-7) + Ethyl oxalyl chloride (4755-77-5) + N,N'-diethylthiourea (105-55-5) → 6-(tert-butylamino)-1,3-diethyl-6-hydroxyl-2-thioxotetrahydropyrimidine-4,5-dione

Conditions	Yield
With water In acetonitrile at 20℃; for 24h; Nef Reaction;	87%

antimony(III) chloride (10025-91-9) + N,N'-diethylthiourea (105-55-5) → ([SbCl2(N,N-diethylthiourea)2]Cl)n

Conditions	Yield
In dichloromethane; acetonitrile for 0.5h;	86.7%

chloroacetic acid (79-11-8) + N,N'-diethylthiourea (105-55-5) → 3-ethyl-2-(ethylimino)-1,3-thiazolidin-4-one (1762-60-3)

Conditions	Yield
In water for 5h; Reflux;	86%
In water at 100℃; for 5h; Green chemistry;	86.4%
In ethanol
Reflux; Green chemistry;

4-chlorobenzaldehyde (104-88-1) + 1-phenyl-acetone (103-79-7) + N,N'-diethylthiourea (105-55-5) → 4-(4-chlorophenyl)-1,3-diethyl-6-methyl-5-phenyl-3,4-dihydropyrimidine-2(1H)-thione

Conditions	Yield
With sodium hydride In ethanol at 75℃; for 3h; Biginelli Pyrimidone Synthesis; regioselective reaction;	86%

formaldehyd (50-00-0) + N,N'-diethylthiourea (105-55-5) + 4-amino-n-butyric acid (56-12-2) → 4-(3,5-diethyl-4-thioxo-1,3,5-triazinan-1-yl)-butanoic acid

Conditions	Yield
In water at 20℃;	85.6%

benzil (134-81-6) + N,N'-diethylthiourea (105-55-5) → 4,5-dihydroxy-1,3-diethyl-4,5-diphenylimidazolidine-2-thione (924851-22-9)

Conditions	Yield
With sodium hydroxide at 180℃; for 0.025h; Microwave irradiation;	85%

diethyl diazirine-3,3-dicarboxylte (76429-94-2) + N,N'-diethylthiourea (105-55-5) → ethyl 1,3-diethyl-5-hydroxy-2-thioxo-2,3-dihydro-1H-imidazole-4-carboxylate

Conditions	Yield
Stage #1: N,N'-diethylthiourea With tetrabutylammonium tetrafluoroborate; magnesium; acetonitrile at -20℃; for 1h; Inert atmosphere; Stage #2: diethyl diazirine-3,3-dicarboxylte at -20℃; Inert atmosphere;	85%

3-hydroxy-2-butanon (513-86-0, 52217-02-4) + N,N'-diethylthiourea (105-55-5) → 1,3-diethyl-4,5-dimethyl-1H-imidazole-2(3H)-thione

Conditions	Yield
In 2-Ethylhexyl alcohol at 185℃; for 20h;	84%
In various solvent(s) at 158℃; for 12h;	61%
In hexan-1-ol Inert atmosphere; Reflux;	60%

N-methylene-tert-butylamine (13987-61-6) + N,N'-diethylthiourea (105-55-5) → 5-tert-Butyl-1,3-diethyl-[1,3,5]triazinane-2-thione (140628-19-9)

Conditions	Yield
for 4h; Heating;	84%

methyl 2-[2-(anilinocarbonyl)-1-diazenyl]-1-cycloheptene-1-carboxylate + N,N'-diethylthiourea (105-55-5) → 2-[3-ethyl-2-(ethylimino)-4-oxo-1-thia-3-azaspiro[4.6]undec-6-ylidene]-1-hydrazinecarboxamide

Conditions	Yield
In methanol at 20℃;	84%

bis(hexafluoroacetylacetonate)platinum(II) + triphenylphosphine (603-35-0) + N,N'-diethylthiourea (105-55-5) → bis(1,3-diethylthiourea)bis(triphenylphosphine)platinum(II) bis(1,1,1,5,5,5-hexafluoro-2,4-pentanedionate)

Conditions	Yield
In dichloromethane addn. of 1,3-diethylthiourea (2 equiv.) to soln. of (Pt(CF3COCHCOCF3)(PPh3)2) (prepd. in situ from (Pt(CF3COCHCOCF3)2) (1 equiv.) and PPh3 (2 equiv.) in CH2Cl2); pptn. on addn. of pentane, product is contaminated by small amts. of (Pt(C2H5NC(S)NHC2H5)(PPh3)2)(CF3COCHCOCF3) (31P-NMR);	84%

ethyl 2-[2-(aminocarbonyl)-1-diazenyl]-1-cyclopentene-1-carboxylate + N,N'-diethylthiourea (105-55-5) → 2-[3-ethyl-2-(ethylimino)-4-oxo-1-thia-3-azaspiro[4.4]non-6-ylidene]-1-hydrazinecarboxamide

Conditions	Yield
In methanol at 20℃;	83%

ethyl 2-[2-(aminocarbonyl)-1-diazenyl]-1-cyclohexene-1-carboxylate + N,N'-diethylthiourea (105-55-5) → 2-[3-ethyl-2-(ethylimino)-4-oxo-1-thia-3-azaspiro[4.5]dec-6-ylidene]-1-hydrazinecarboxamide

Conditions	Yield
In methanol at 20℃;	83%

acetylenedicarboxylic acid diethyl ester (762-21-0) + N,N'-diethylthiourea (105-55-5) → ethyl 3-ethyl-2-(ethylimino)-3,4-dihydro-4-oxo-2H-1,3-thiazine-6-carboxylate (1220968-91-1)

Conditions	Yield
With triphenylphosphine In water at 50℃;	83%

Upstream product

• 542-85-8 Ethyl isothiocyanate 
• 75-15-0 carbon disulfide 
• 75-04-7 ethylamine 
• 100-65-2 N-Phenylhydroxylamine 
• 593-77-1 N-Methylhydroxylamine 
• 462-60-2 N-carbamoylglycine 
• 924851-22-9 4,5-dihydroxy-1,3-diethyl-4,5-diphenylimidazolidine-2-thione 
• 67-63-0 isopropyl alcohol 
• 17303-54-7 ureidoacetylaminoethanoic acid 
• 2609-10-1 grateloupine 
• 462-88-4 N-carbamoyl-β-alanine 
• 67-56-1 methanol 
• 116849-51-5 S-ethyl O-phenyl dithiocarbonate 
• 998-98-1 N-ethyl O-ethyl thiocarbamate 

Downstream Products

• 3120-51-2 6-amino-1,3-diethyl-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one 
• 82214-17-3 C₁₃H₁₉N₃S₂ 
• 122-56-5 tributyl borane 
• 84185-22-8 2,6-Di-n-butyl-3,5-diethyl-2,3,5,6-tetrahydro-4H-1,3,5,2,6-thiadiazadiborin-4-thion 
• 84185-18-2 3,5-Diethyl-2,3,5,6-tetrahydro-2,6-diphenyl-4H-1,3,5,2,6-thidiazadiborin-4-thion 
• 84185-27-3 1,5-Diethyl-2,3,4,5-tetrahydro-2,4-diphenyl-1,3,5,2,4-triazadiborin-6(1H)thion 
• 81233-37-6 1,3,5-Triethyl-2,6-diphenyl-1,3,5-triaza-2,6-dibora-cyclohexanthion-4 
• 1096570-73-8 C₁₉H₂₀N₂S 
• 1204185-62-5 cis-1,3-diethyl-4,5-dihydroxy-4,5-diphenylimidazolidine-2-thione 
• 145036-41-5 {Pt(C₂H₅NC(S)NHC₂H₅)(P(C₆H₅)3)2}⁽¹⁺⁾*CF₃COCHCOCF₃^(1-)={Pt(C₂H₅NC(S)NHC₂H₅)(P(C₆H₅)3)2}(CF₃COCHCOCF₃) 
• 145036-45-9 {Pt(C₂H₅NC(S)NC₂H₅)(P(C₆H₅)3)2} 
• 90388-87-7 (C₆H₅)2SnCl₂(NHC₂H₅CSNHC₂H₅)2 

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The mechanisms of hydrolysis of alkyl N-alkylthioncarbamate esters at 100°C

The hydrolysis of ethyl N-ethylthioncarbamate (ETE) at 100°C was studied in the range of 7 mol/L HCl to 4 mol/L NaOH. The pH-rate profile showed that the hydrolysis occurred through specific acid catalysis at pH 6.5. The Hammett acidity plot and the excess acidity plot against X were linear. The Bunnett-Olsen plot gave a negative slope indicating that the conjugate acid was less hydrated than the neutral substrate. It was concluded that the acid hydrolysis occurred by an Al mechanism. The neutral species hydrolyzed with general base catalysis shown by the Bronsted plot with β = 0.48 ± 0.04. Water acted as a general base catalyst with (pseudo-)first-order rate constant, kN = 3.06 × 10-7 s-1. At pH > 6.5 the rate constants increased, reaching a plateau at high basicity. The basic hydrolysis rate constant of ethyl N,N-diethylthioncarbamate, which must react by a BAc2 mechanism, increased linearly at 1-3 mol/L NaOH with a second-order rate constant, k2 = 2.3 × 10-4 (mol/L)-1 s-1, which was 10 times slower than that expected for ETE. Experiments of ETE in 0.6 mol/L NaOH with an excess of ethylamine led to the formation of diethyl thiourea, presenting strong evidence that the basic hydrolysis occurred by the E1cb mechanism. In the rate-determining step, the E1cb mechanism involved the elimination of ethoxide ion from the thioncarbamate anion, producing an isothiocyanate intermediate that decomposed rapidly to form ethylamine, ethanol, and COS.

Green Process Development for the Synthesis of Aliphatic Symmetrical N,N ′-Disubstituted Thiourea Derivatives in Aqueous Medium

A highly efficient green process for the synthesis of N,N′-disubstituted aliphatic thiourea derivatives using primary aliphatic amines and carbon disulfide in an aqueous medium at room temperature via a nonisothiocyanate route is described. This protocol illustrates the rapid preparation of N,N′-disubstituted aliphatic thiourea derivatives in excellent yields with some advantages such as no catalyst and simple workup without any side product formation. Moreover, the new route is concise, does not require chromatography, and is adaptable to pilot-scale preparation. GRAPHICAL ABSTRACT.

α-Thioureidoalkylation of functionally substituted ureas: I. Tandem cyclization and esterification in reactions of N-(carboxyalkyl)ureas with 1,3-dialkyl-4,5-dihydroxy-4,5-diphenylimidazolidine-2-thiones in alcohols

Acid-catalyzed reactions of N-(carboxyalkyl)ureas with 1,3-dialkyl-4,5- dihydroxy-4,5-diphenylimidazolidine- 2-thiones in methanol or propan-2-ol led to the formation of previously unknown ω-(4,6-dialkyl- 2-oxo-3a,6a-diphenyl- 5-thioxooctahydroimidazo[4,5-d]imidazol-1-yl)alkanoic acids and their methyl and isopropyl esters. The structure of some esters was proved by X-ray analysis. Methyl (4,6-diethyl-2-oxo-3a,6adiphenyl- 5-thioxooctahydroimidazo[4,5-d] imidazol-1-yl)acetate showed anxiolytic effect. Pleiades Publishing, Ltd., 2011.