52599-24-3

Basic information

• Product Name: N-T-BUTYL-N'-ISOPROPYLTHIOUREA
• Synonyms: N-T-BUTYL-N'-ISOPROPYLTHIOUREA;1-Isopropyl-3-Tert-Butylthiourea;N-T-BUTYL-N'-ISOPROP;1-(tert-butyl)-3-isopropylthiourea
• CAS NO: 52599-24-3
• Molecular Formula: C₈H₁₈N₂S
• Molecular Weight: 174.31
• Mol File: 52599-24-3.mol
• Article Data: 7

Chemical Properties

• Melting Point: 150-152℃
• Boiling Point: 215.3±23.0 °C(Predicted)
• Appearance: /
• Density: 0.949±0.06 g/cm3(Predicted)
• PKA: 14.31±0.70(Predicted)
• CAS DataBase Reference: N-T-BUTYL-N'-ISOPROPYLTHIOUREA(CAS DataBase Reference)
• NIST Chemistry Reference: N-T-BUTYL-N'-ISOPROPYLTHIOUREA(52599-24-3)
• EPA Substance Registry System: N-T-BUTYL-N'-ISOPROPYLTHIOUREA(52599-24-3)

Safety Data

• Hazardous Substances Data: 52599-24-3(Hazardous Substances Data)

Usage

General Description

N-T-Butyl-N'-Isopropylthiourea is a chemical compound that falls under the class of thioureas. Thioureas are organic compounds sharing a common functional group characterized by nitrogen, sulfur and carbon atoms. The term 'thiourea' generally refers to a specific molecule having two amine groups attached to a carbonyl group with a sulfur atom replacing the carbonyl oxygen. The structure of N-T-Butyl-N'-Isopropylthiourea therefore follows this structure. Its properties, usage, or safety profile will depend heavily on its synthesis, material handling, and specific applications, which isn't specified in the available literature. As with other chemicals alike, guidelines and regulations should be followed when handling or incorporating it into any processes or products.

Synthetic route

tert-butyl isothiocyanate (590-42-1) + diisopropylethylamine (DIEA) + isopropylamine (75-31-0) → N-tert-butyl-N'-isopropylthiourea (52599-24-3)

Conditions	Yield
In dichloromethane	52%
In dichloromethane	52%

tert-butyl isothiocyanate (590-42-1) + isopropylamine (75-31-0) → N-tert-butyl-N'-isopropylthiourea (52599-24-3)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 2h;	52%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 2h;	52%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 2h;	52%
In chlorobenzene at 10 - 30℃; for 1h; Green chemistry;

carbon disulfide (75-15-0) + N,N,N′,N′-tetramethyl-N″-tert-butylguanidine (29166-72-1) + isopropylamine (75-31-0) → 1,1,3,3-tetramethyl-2-thiourea (2782-91-4) + N-tert-butyl-N'-isopropylthiourea (52599-24-3)

Conditions	Yield
1.) 0.5 h, 2.) room temperature, 1.5 h; Yield given. Multistep reaction. Yields of byproduct given;

N-tert-butyl-N'-isopropylthiourea (52599-24-3) + N-Chloromethyl-N-phenylcarbamoyl chloride (52123-54-3) → buprofezin (69327-76-0)

Conditions	Yield
Stage #1: N-Chloromethyl-N-phenylcarbamoyl chloride With dipotassium peroxodisulfate; 3,6-dimethyl-3,6-dihydroperoxy-4,5-dioxaoctane at 40 - 45℃; Flow reactor; Large scale; Stage #2: N-tert-butyl-N'-isopropylthiourea With tetradecyltrimethylammonium chloride; calcium hydroxide at 15 - 50℃; Reagent/catalyst; Temperature; Flow reactor; Large scale;	92.3%
With sodium acetate In water; toluene at 30 - 45℃; for 2h; Temperature; Reagent/catalyst;	87%
With sodium hydrogencarbonate In water; chlorobenzene at 0 - 30℃; for 5.5h; Green chemistry;
With ammonia In 1,4-dioxane at 10 - 40℃; for 5h; Reagent/catalyst;

N-tert-butyl-N'-isopropylthiourea (52599-24-3) → 1-isopropylthiourea (1719-76-2)

Conditions	Yield
With hydrogenchloride In water for 0.666667h; Heating / reflux;	90%
In hydrogenchloride	90%
In hydrogenchloride	90%
With hydrogenchloride In water for 0.666667h; Heating / reflux;	90%
Stage #1: N-tert-butyl-N'-isopropylthiourea With hydrogenchloride; water for 0.666667h; Heating / reflux; Stage #2: With water; sodium hydrogencarbonate at 0℃; pH=9.5; Saturated solution;	90%

N-chloromethyl-N-(p-chlorophenyl)carbamoyl chloride + N-tert-butyl-N'-isopropylthiourea (52599-24-3) → 2-t-Butylimino-3-isopropyl-5-(p-chlorophenyl)-tetrahydro-1,3,5-thiadiazin-4-one

Conditions	Yield
With potassium hydroxide In benzene	62%

1,3,5-tris(o-isopropyl)phenyl-hexahydro-s-triazine (69330-83-2) + N-tert-butyl-N'-isopropylthiourea (52599-24-3) + trichloromethyl chloroformate (503-38-8) → 2-tert-butylimino-3-isopropyl-5-(2-isopropyl-phenyl)-[1,3,5]thiadiazinan-4-one (69329-73-3)

Conditions	Yield
With potassium hydroxide In tetrahydrofuran; benzene	52%

N-tert-butyl-N'-isopropylthiourea (52599-24-3) → N,N′-diisopropylcarbodiimide (55546-43-5)

Conditions	Yield
With lead dioxide In water Heating;	50%

N-tert-butyl-N'-isopropylthiourea (52599-24-3) + 1,3,5-tris(p-tolyl)hexahydro-s-triazine (6639-47-0) + trichloromethyl chloroformate (503-38-8) → 2-t-butylimino-3-isopropyl-5-p-tolyltetrahydro-1,3,5-thiadiazin-4-one

Conditions	Yield
With sodium hydroxide In tetrahydrofuran; benzene	45%

1,3,5-tris(2,3-dimethylphenyl)-hexahydro-s-triazine + N-tert-butyl-N'-isopropylthiourea (52599-24-3) + trichloromethyl chloroformate (503-38-8) → 2-t-butylimino-3-isopropyl-5-(2,3-dimethylphenyl)-tetrahydro-1,3,5-thiadiazin-4-one

Conditions	Yield
With sodium hydroxide	45%

oxalyl dichloride (79-37-8) + N-tert-butyl-N'-isopropylthiourea (52599-24-3) → 1-tert-Butyl-3-isopropyl-2-thioxoimidazolidin-4,5-dion

Conditions	Yield
In toluene for 1h; Heating;	42%

1,3,5-tris(2,4-dimethylphenyl)-hexahydro-s-triazine + N-tert-butyl-N'-isopropylthiourea (52599-24-3) + trichloromethyl chloroformate (503-38-8) → 2-t-butylimino-3-isopropyl-5-(2,4-dimethylphenyl)-tetrahydro-1,3,5-thiadiazin-4-one

Conditions	Yield
With sodium hydroxide	18%

hexahydro-1,3,5-tris(p-ethylphenyl)-s-triazine + N-tert-butyl-N'-isopropylthiourea (52599-24-3) + trichloromethyl chloroformate (503-38-8) → 2-t-butylimino-3-isopropyl-5-(p-ethylphenyl)-tetrahydro-1,3,5-thiadiazin-4-one

Conditions	Yield
With sodium hydroxide	17%

N-tert-butyl-N'-isopropylthiourea (52599-24-3) + 2,6-dimethyl-N-methylene benzamine (35203-02-2) + trichloromethyl chloroformate (503-38-8) → 2-t-butylimino-3-isopropyl-5-(2,6-dimethylphenyl)tetrahydro-1,3,5-thiadiazin-4-one

Conditions	Yield
With sodium hydroxide	7%

N-tert-butyl-N'-isopropylthiourea (52599-24-3) → 1-tert-Butyl-3-isopropylimidazolidin-2,4,5-trion

Conditions	Yield
Multi-step reaction with 2 steps 1: 42 percent / toluene / 1 h / Heating 2: 88 percent / Hg(OAc)2 / CHCl3 / 1 h / 25 °C View Scheme

aqueous potassium hydroxide + N-tert-butyl-N'-isopropylthiourea (52599-24-3) + N-Chloromethyl-N-phenylcarbamoyl chloride (52123-54-3) → 2-tert-butylimino-3-isopropyl-5-phenyl-3,4,5,6-tetrahydro-2H-1,3,5-thiadiazin-4-one

Conditions	Yield
In N-methyl-acetamide; acetone

N-chloromethyl-N-(p-fluorophenyl)-carbamoyl chloride + N-tert-butyl-N'-isopropylthiourea (52599-24-3) + N,N-dimethylthiourea (534-13-4) → 2-tert-butylimino-5-(4-fluoro-phenyl)-3-isopropyl-[1,3,5]thiadiazinan-4-one (69329-12-0)

Conditions	Yield
With sodium hydroxide In water; acetone; benzene

N-tert-butyl-N'-isopropylthiourea (52599-24-3) → 2-t-butylimino-3-isopropyl-5-(o-chlorophenyl)-tetrahydro-1,3,5-thiadiazin-4-one

Conditions	Yield
	2.3 g (70%)

N-chloromethyl-N-(m-chlorophenyl)-carbamoyl chloride + N-tert-butyl-N'-isopropylthiourea (52599-24-3) → 2-t-Butylimino-3-isopropyl-5-(m-chlorophenyl)-tetrahydro-1,3,5-thiadiazin-4-one

Conditions	Yield
With sodium hydroxide In benzene

N-(3,4-dichlorophenyl)-N-chloromethylcarbamoyl chloride + N-tert-butyl-N'-isopropylthiourea (52599-24-3) → 2-t-Butylimino-3-isopropyl-5-(3,4-dichlorophenyl)-tetrahydro-1,3,5-thiadiazin-4-one

Conditions	Yield
With sodium hydroxide In benzene

Upstream product

• 590-42-1 tert-butyl isothiocyanate 
• 75-31-0 isopropylamine 
• 75-15-0 carbon disulfide 
• 29166-72-1 N,N,N′,N′-tetramethyl-N″-tert-butylguanidine 

Downstream Products

• 953030-84-7 2-tert-butylimino-3-isopropyl-5-phenyl-3,4,5,6-tetrahydro-2H-1,3,5-thiadiazin-4-one 
• 69327-76-0 buprofezin 
• 69329-12-0 2-tert-butylimino-5-(4-fluoro-phenyl)-3-isopropyl-[1,3,5]thiadiazinan-4-one 
• 69329-73-3 2-tert-butylimino-3-isopropyl-5-(2-isopropyl-phenyl)-[1,3,5]thiadiazinan-4-one 
• 1719-76-2 1-isopropylthiourea 

Relevant articles and documents

Preparation method of buprofezin

The invention provides a preparation method of buprofezin, comprising the steps of 1), adding sodium thiocyanate and water into an esterification kettle until dissolution; adding tertiary butanol andhydrochloric acid to obtain a mixed ester; allowing transposition and catalytic reaction to obtain t-butyl isothiocyanate; 2), adding the t-butyl isothiocyanate into chlorobenzene, stirring, dropwiseadding isopropyl amine to obtain 1-isopropyl-3-tert-butylthiourea solution; 3), adding N-methylaniline into chlorobenzene; introducing carbonyl chloride and chlorine gas in sequence to obtain N-chloromethyl-N-benzenecarbamoylchloride solution; 4), adding sodium bicarbonate into water, and adding the resultant into chlorobenzene; adding the 1-isopropyl-3-tert-butylthiourea solution; dropwise addingthe N-chloromethyl-N-benzenecarbamoylchloride solution, filtering, allowing layering, performing high-vacuum steaming to remove the chlorobenzene, crystallizing, centrifuging, and drying to obtain buprofezin. The substitutive average yield of the preparation process of buprofezin reaches 90% and above; the content of finished buprofezin reaches 98.0% and above; the preparation process is free ofammonia nitrogen wastewater.

Macrocylic Inhibitors of Hepatitis C Virus

Compounds of the formula I: and N-oxides, salts, and stereoisomers thereof wherein A is OR1, NHS(═O)pR2; wherein; R1 is hydrogen, C1-C6alkyl, C0-C3alkylenecarbocyclyl, C0-C3alkylene-heterocyclyl;R2 is C1-C6alkyl, C0-C3alkylenecarbocyclyl, C0-C3alkyleneheterocyclyl;p is independently 1 or 2;n is 3, 4, 5 or 6; — denotes an optional double bond;L is N or CRz; Rz is H or forms a double bond with the asterisked carbon;Rq is H or when L is CRz, Rq can also be C1-C6alkyl;Rr is quinazolinyl, optionally substituted with one two or three substituents each independently selected from C1-C6 alkyl, C1-C6alkoxy, hydroxyl, halo, haloC1-C6alkyl, amino, mono- or dialkylamino, mono- or dialkylaminocarbonyl, C1-C6alkyl-carbonylamino, C0-C3alkylenecarbocyclyl and C0-C3 alkyleneheterocyclyl;R5 is hydrogen, C1-C6alkyl, C1-C6alkoxyC1-C6alkyl or C3-C7cycloalkyl;R6 is hydrogen, C1-C6alkyl, C1-C6alkoxy, C0-C3alkylenecarbocyclyl, C0-C3alkylene-heterocyclyl, hydroxy, bromo, chloro or fluoro have utility in the treatment or prophylaxis of flaviviral infections such as HCV

HCV NS-3 serine protease inhibitors

HCV inhibitors, compositions comprising these compounds as active ingredient, as well as processes for preparing these compounds, of formula: wherein A is