61832-41-5

Basic information

• Product Name: N-Methyl-1-(methylthio)-2-nitroethylen-1-amine
• Synonyms: N-Methyl-1-(methylth;Methyl (1Z)-N-Methyl-2-nitroethaniMidothioate;1-(Methylthio)-2-nitro-N-MethylethyleneaMine;2-(Methylthio)-2-(MethylaMino)-1-nitroethene;Nizatidine EP IMpurity B;(E)-N-Methyl-1-(Methylthio)-2-nitroethenaMine;1-(Methylamino)-1-(methylthio)-2-nitroethylene, N-Methyl-1-(methylsulphanyl)-2-nitroethenamine;N-Methyl-1-(methylthio)-2-nitroethenamine
• CAS NO: 61832-41-5
• Molecular Formula: C₄H₈N₂O₂S
• Molecular Weight: 149.19
• EINECS: 263-266-9
• Product Categories: Sulfur Compounds;Intermediates;Sulfur & Selenium Compounds;PHARMACEUTICAL INTERMEDIATES;Anilines, Aromatic Amines and Nitro Compounds;Amines;(intermediate of ranitidine);Organic Building Blocks;Sulfides/Disulfides
• Mol File: 61832-41-5.mol
• Article Data: 15

Chemical Properties

• Melting Point: 112-118 °C(lit.)
• Boiling Point: 236.5 °C at 760 mmHg
• Flash Point: 96.8 °C
• Appearance: /
• Density: 1.199 g/cm³
• Vapor Pressure: 0.168mmHg at 25°C
• Refractive Index: 1.533
• PKA: 0.86±0.70(Predicted)
• BRN: 2828017
• CAS DataBase Reference: N-Methyl-1-(methylthio)-2-nitroethylen-1-amine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Methyl-1-(methylthio)-2-nitroethylen-1-amine(61832-41-5)
• EPA Substance Registry System: N-Methyl-1-(methylthio)-2-nitroethylen-1-amine(61832-41-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• RIDADR: UN 3335
• WGK Germany: 3
• Hazardous Substances Data: 61832-41-5(Hazardous Substances Data)

Usage

Chemical Properties

Yellow Solid

Uses

Different sources of media describe the Uses of 61832-41-5 differently. You can refer to the following data:
1. Intermediate in the preparation of Ranitidine and Nizatidine.
2. (E) N-methyl-1-(methylthio)-2-nitroethenamine) (NMSM) may be used for the following syntheses:pyrano[2,3-c]pyrazol-6-amines6-methoxy-N-methyl-3-nitro-4-nitromethyl-4H-chromen-2-amine

InChI:InChI=1/C4H8N2O2S/c1-5-4(9-2)3-6(7)8/h3H2,1-2H3/b5-4-

Synthetic route

methylamine (74-89-5) + 1,1-di(methylsulfanyl)-2-nitroethylene (13623-94-4) → (E-)-N-methyl-1-(methylthio)-2-nitroethanamine (61832-41-5)

Conditions	Yield
In ethanol for 5h; Reflux;	75%

methylamine hydrochloride (593-51-1) + 1,1-di(methylsulfanyl)-2-nitroethylene (13623-94-4) → (E-)-N-methyl-1-(methylthio)-2-nitroethanamine (61832-41-5)

Conditions	Yield
With potassium carbonate In dichloromethane

1-(n-methylsulfinyl)-1-(n-methylthio)-2-nitroethene (61832-49-3) → (E-)-N-methyl-1-(methylthio)-2-nitroethanamine (61832-41-5)

Conditions	Yield
With methylamine In methanol

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine (61832-41-5) + benzaldehyde (100-52-7) → N,1-dimethyl-6-(methylthio)-3,5-dinitro-4-phenyl-1,4-dihydropyridin-2-amine (1620024-38-5)

Conditions	Yield
With toluene-4-sulfonic acid In water at 20℃; for 0.25h; Catalytic behavior; Solvent; Reagent/catalyst; Green chemistry;	98%
In neat (no solvent) at 100℃; for 0.166667h; Temperature; Solvent; Reagent/catalyst; Microwave irradiation; Green chemistry;	94%
With 2-aminopyridine In ethanol at 80℃; for 5h;	92%

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine (61832-41-5) + 3-methoxy-2-hydroxybenzaldehyde (148-53-8) → N-[8-methoxy-4-(methylsulfanyl)-3-nitro-4H-2-chromenyl]-N-methylamine (1173429-63-4)

Conditions	Yield
With cholin hydroxide In water at 20℃; for 5h; Green chemistry;	96%
Stage #1: 3-methoxy-2-hydroxybenzaldehyde With 1,8-diazabicyclo[5.4.0]undec-7-ene In methanol at 20℃; Stage #2: (E-)-N-methyl-1-(methylthio)-2-nitroethanamine In methanol at 20℃; for 15h;	85%

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine (61832-41-5) + ethyl acetoacetate (141-97-9) + 2-methylphenyl aldehyde (529-20-4) + phenylhydrazine (100-63-0) → 4-(2-methylphenyl)-N,3-dimethyl-5-nitro-1-phenyl-1,4-dihydropyrano[2,3-c]pyrazol-6-amine

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In ethanol Reflux;	96%

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine (61832-41-5) + 3,4,5-trimethoxy-benzaldehyde (86-81-7) + β-naphthol (135-19-3) → 1-(3,4,5-trimethoxyphenyl)-N-methyl-2-nitro-1H-benzo[f]chromen-3-amine

Conditions	Yield
In ethanol; water at 60℃; for 0.583333h; Green chemistry;	96%

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine (61832-41-5) + 4-methoxy-benzaldehyde (123-11-5) + β-naphthol (135-19-3) → 1-(4-methoxyphenyl)-N-methyl-2-nitro-1H-benzo[f]chromen-3-amine

Conditions	Yield
In ethanol; water at 60℃; for 0.6h; Green chemistry;	96%

2,7-Dihydroxynaphthalene (582-17-2) + (E-)-N-methyl-1-(methylthio)-2-nitroethanamine (61832-41-5) + 4-methoxy-benzaldehyde (123-11-5) → 1-(4-methoxyphenyl)-3-(methylamino)-2-nitro-1H-benzo[f]chromen-9-ol

Conditions	Yield
In ethanol; water at 60℃; for 0.583333h; Green chemistry;	96%

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine (61832-41-5) + 4-ethoxybenzaldehyde (10031-82-0) + β-naphthol (135-19-3) → 1-(4-ethoxyphenyl)-N-methyl-2-nitro-1H-benzo[f]chromen-3-amine

Conditions	Yield
In ethanol; water at 60℃; for 0.583333h; Green chemistry;	96%

piperonal (120-57-0) + (E-)-N-methyl-1-(methylthio)-2-nitroethanamine (61832-41-5) + β-naphthol (135-19-3) → 1-(benzo[d][1,3]dioxol-6-yl)-N-methyl-2-nitro-1H-benzo[f]chromen-3-amine

Conditions	Yield
In ethanol; water at 60℃; for 0.616667h; Green chemistry;	96%

1H-benzimidazol-2-amine (934-32-7) + (E-)-N-methyl-1-(methylthio)-2-nitroethanamine (61832-41-5) + 4-methyl-benzaldehyde (104-87-0) → N-methyl-3-nitro-4-(p-tolyl)-4,10-dihydrobenzo[4,5]imidazo[1,2-a]pyrimidin-2-amine

Conditions	Yield
With polyethylene glycol methacrylate-grafted tetraethylene glycol-bridged dicationic imidazolium based ionic liquid In neat (no solvent) at 80℃; Green chemistry;	96%
With toluene-4-sulfonic acid In ethanol at 80℃; for 3h;	91%

1H-benzimidazol-2-amine (934-32-7) + (E-)-N-methyl-1-(methylthio)-2-nitroethanamine (61832-41-5) + 4-ethoxybenzaldehyde (10031-82-0) → 4-(4-ethoxyphenyl)-N-methyl-3-nitro-4,10-dihydrobenzo[4,5]imidazo[1,2-a]pyrimidin-2-amine

Conditions	Yield
With polyethylene glycol methacrylate-grafted tetraethylene glycol-bridged dicationic imidazolium based ionic liquid In neat (no solvent) at 80℃; Green chemistry;	96%

1H-benzimidazol-2-amine (934-32-7) + (E-)-N-methyl-1-(methylthio)-2-nitroethanamine (61832-41-5) + 4-methoxy-benzaldehyde (123-11-5) → 4-(4-methoxyphenyl)-N-methyl-3-nitro-4,10-dihydrobenzo[4,5]imidazo[1,2-a]pyrimidin-2-amine

Conditions	Yield
With polyethylene glycol methacrylate-grafted tetraethylene glycol-bridged dicationic imidazolium based ionic liquid In neat (no solvent) at 80℃; for 0.333333h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; Green chemistry;	96%
With toluene-4-sulfonic acid In ethanol at 80℃; for 3h;	91%

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine (61832-41-5) + 4-chlorobenzaldehyde (104-88-1) + Benzoylacetonitrile (614-16-4) → 6-(methylamino)-4-(4-chlorophenyl)-5-nitro-2-phenyl-4H-pyran-3-carbonitrile

Conditions	Yield
Stage #1: 4-chlorobenzaldehyde; Benzoylacetonitrile With triethylamine In ethanol at 20℃; for 0.0833333 - 0.166667h; Stage #2: (E-)-N-methyl-1-(methylthio)-2-nitroethanamine In ethanol for 1.5h; Reflux;	95%
With triethylamine In ethanol for 1.5h; Reflux; regioselective reaction;	93%

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine (61832-41-5) + 4-chlorobenzaldehyde (104-88-1) + 3-(1H-indol-3-yl)-3-oxo-propionitrile (20356-45-0) → 2-(1H-indol-3-yl)-6-(methylamino)-5-nitro-4-(4-chlorophenyl)-4H-pyran-3-carbonitrile (1463535-38-7)

Conditions	Yield
With triethylamine In ethanol for 1.5h; Solvent; Reagent/catalyst; Reflux; regioselective reaction;	95%
With indium(III) chloride for 0.0833333h; Microwave irradiation; Sealed tube; chemoselective reaction;	86%

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine (61832-41-5) + Benzoylacetonitrile (614-16-4) + 4-bromo-benzaldehyde (1122-91-4) → 6-(methylamino)-4-(4-bromophenyl)-5-nitro-2-phenyl-4H-pyran-3-carbonitrile (1463535-58-1)

Conditions	Yield
With triethylamine In ethanol for 1.5h; Reflux; regioselective reaction;	95%

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine (61832-41-5) + ethyl acetoacetate (141-97-9) + 4-bromo-benzaldehyde (1122-91-4) + phenylhydrazine (100-63-0) → 4-(4-bromophenyl)-N,3-dimethyl-5-nitro-1-phenyl-1,4-dihydropyrano[2,3-c]pyrazol-6-amine

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In ethanol Reflux;	95%

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine (61832-41-5) + ethyl acetoacetate (141-97-9) + 3,4,5-trimethoxy-benzaldehyde (86-81-7) + phenylhydrazine (100-63-0) → 4-(3,4,5-trimethoxyphenyl)-N,3-dimethyl-5-nitro-1-phenyl-1,4-dihydropyrano[2,3-c]pyrazol-6-amine

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In ethanol Reflux;	95%

1-prop-2-ynyl-1H-indole-2,3-dione (4290-87-3) + (E-)-N-methyl-1-(methylthio)-2-nitroethanamine (61832-41-5) + edaravone (89-25-8) → C24H19N5O4 (1609627-39-5)

Conditions	Yield
In water at 80℃; Solvent; Green chemistry;	95%
With indium(III) chloride In ethanol for 7h; Reflux; Green chemistry; regioselective reaction;	90%

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine (61832-41-5) + 2-methylphenyl aldehyde (529-20-4) + β-naphthol (135-19-3) → N-methyl-2-nitro-1-o-tolyl-1H-benzo[f]chromen-3-amine

Conditions	Yield
In ethanol; water at 60℃; for 0.633333h; Green chemistry;	95%

2,7-Dihydroxynaphthalene (582-17-2) + (E-)-N-methyl-1-(methylthio)-2-nitroethanamine (61832-41-5) + 3-methoxy-benzaldehyde (591-31-1) → 1-(3-methoxyphenyl)-3-(methylamino)-2-nitro-1H-benzo[f]chromen-9-ol

Conditions	Yield
In ethanol; water at 60℃; for 0.633333h; Green chemistry;	95%

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine (61832-41-5) + 4-bromo-benzaldehyde (1122-91-4) + 2,3-naphthalenediol (92-44-4) → 1-(4-bromophenyl)-3-(methylamino)-2-nitro-1H-benzo[f]chromen-5-ol

Conditions	Yield
In ethanol; water at 60℃; for 0.666667h; Green chemistry;	95%

2,7-Dihydroxynaphthalene (582-17-2) + (E-)-N-methyl-1-(methylthio)-2-nitroethanamine (61832-41-5) + 4-bromo-benzaldehyde (1122-91-4) → 1-(4-bromophenyl)-3-(methylamino)-2-nitro-1H-benzo[f]chromen-9-ol

Conditions	Yield
In ethanol; water at 60℃; for 0.633333h; Green chemistry;	95%

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine (61832-41-5) + 4-chlorobenzaldehyde (104-88-1) + β-naphthol (135-19-3) → 1-(4-chlorophenyl)-N-methyl-2-nitro-1H-benzo[f]chromen-3-amine

Conditions	Yield
In ethanol; water at 60℃; for 0.583333h; Green chemistry;	95%

2,7-Dihydroxynaphthalene (582-17-2) + (E-)-N-methyl-1-(methylthio)-2-nitroethanamine (61832-41-5) + 4-fluorobenzaldehyde (459-57-4) → 1-(4-fluorophenyl)-3-(methylamino)-2-nitro-1H-benzo[f]chromen-9-ol

Conditions	Yield
In ethanol; water at 60℃; for 0.616667h; Green chemistry;	95%

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine (61832-41-5) + 4-ethoxybenzaldehyde (10031-82-0) + 2,3-naphthalenediol (92-44-4) → 1-(4-ethoxyphenyl)-3-(methylamino)-2-nitro-1H-benzo[f]chromen-5-ol

Conditions	Yield
In ethanol; water at 60℃; for 0.633333h; Green chemistry;	95%

2,7-Dihydroxynaphthalene (582-17-2) + (E-)-N-methyl-1-(methylthio)-2-nitroethanamine (61832-41-5) + 4-ethoxybenzaldehyde (10031-82-0) → 1-(4-ethoxyphenyl)-3-(methylamino)-2-nitro-1H-benzo[f]chromen-9-ol

Conditions	Yield
In ethanol; water at 60℃; for 0.6h; Green chemistry;	95%

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine (61832-41-5) + 3-Chlorobenzaldehyde (587-04-2) + β-naphthol (135-19-3) → 1-(3-chlorophenyl)-N-methyl-2-nitro-1H-benzo[f]chromen-3-amine

Conditions	Yield
In ethanol; water at 60℃; for 0.633333h; Green chemistry;	95%

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine (61832-41-5) + (4-isopropylbenzaldehyde) (122-03-2) + β-naphthol (135-19-3) → 1-(4-isopropylphenyl)-N-methyl-2-nitro-1H-benzo[f]chromen-3-amine

Conditions	Yield
In ethanol; water at 60℃; for 0.633333h; Green chemistry;	95%

thiophene-2-carbaldehyde (98-03-3) + 2,7-Dihydroxynaphthalene (582-17-2) + (E-)-N-methyl-1-(methylthio)-2-nitroethanamine (61832-41-5) → 3-(methylamino)-2-nitro-1-(thiophen-2-yl)-1H-benzo[f]chromen-9-ol

Conditions	Yield
In ethanol; water at 60℃; for 0.666667h; Mechanism; Solvent; Temperature; Time; Green chemistry;	95%

1H-benzimidazol-2-amine (934-32-7) + (E-)-N-methyl-1-(methylthio)-2-nitroethanamine (61832-41-5) + 4-bromo-benzaldehyde (1122-91-4) → 4-(4-bromophenyl)-N-methyl-3-nitro-4,10-dihydrobenzo[4,5]imidazo[1,2-a]pyrimidin-2-amine

Conditions	Yield
With polyethylene glycol methacrylate-grafted tetraethylene glycol-bridged dicationic imidazolium based ionic liquid In neat (no solvent) at 80℃; Green chemistry;	95%
With toluene-4-sulfonic acid In ethanol at 80℃; for 3h;	89%

1H-benzimidazol-2-amine (934-32-7) + (E-)-N-methyl-1-(methylthio)-2-nitroethanamine (61832-41-5) + 4-fluorobenzaldehyde (459-57-4) → 4-(4-fluorophenyl)-N-methyl-3-nitro-4,10-dihydrobenzo[4,5]imidazo[1,2-a]pyrimidin-2-amine

Conditions	Yield
With polyethylene glycol methacrylate-grafted tetraethylene glycol-bridged dicationic imidazolium based ionic liquid In neat (no solvent) at 80℃; Green chemistry;	95%
With toluene-4-sulfonic acid In ethanol at 80℃; for 4h;	90%

Upstream product

• 74-89-5 methylamine 
• 13623-94-4 1,1-di(methylsulfanyl)-2-nitroethylene 
• 61832-49-3 1-(n-methylsulfinyl)-1-(n-methylthio)-2-nitroethene 
• 593-51-1 methylamine hydrochloride 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 75-52-5 nitromethane 
• 18805-25-9 methyl carbonimidodithioic acid dimethyl ester 

Downstream Products

• 1173429-51-0 N-[6-ethyl-4-(methylsulfanyl)-3-nitro-4H-2-chromenyl]-N-methylamine 
• 1173429-61-2 N-[7-(benzyloxy)-4-(methylsulfanyl)-3-nitro-4H-2-chromenyl]-N-methylamine 
• 1233536-62-3 C₁₄H₁₇N₃O₂ 
• 1233536-63-4 C₁₃H₁₅N₃O₂ 
• 1438418-05-3 4-(2-chlorophenyl)-6-methyl-2-(methylamino)-3-nitro-4H-pyrano[3,2-c]quinolin-5(6H)-one 
• 1438418-06-4 4-(3-fluorophenyl)-6-methyl-2-(methylamino)-3-nitro-4H-pyrano[3,2-c]quinolin-5(6H)-one 
• 1438418-07-5 4-(3-bromophenyl)-6-methyl-2-(methylamino)-3-nitro-4H-pyrano[3,2-c]quinolin-5(6H)-one 
• 1438418-08-6 6-methyl-2-(methylamino)-3-nitro-4-(4-nitrophenyl)-4H-pyrano[3,2-c]quinolin-5(6H)-one 
• 1438418-10-0 4-(2,3-dichlorophenyl)-6-methyl-2-(methylamino)-3-nitro-4H-pyrano[3,2-c]quinolin-5(6H)-one 
• 1438418-11-1 4-(2,4-dichlorophenyl)-6-methyl-2-(methylamino)-3-nitro-4H-pyrano[3,2-c]quinolin-5(6H)-one 
• 1438418-12-2 4-(2,5-dimethoxyphenyl)-6-methyl-2-(methylamino)-3-nitro-4H-pyrano[3,2-c]quinolin-5(6H)-one 
• 1438417-98-1 4-(4-chlorophenyl)-6-methyl-2-(methylamino)-3-nitro-4H-pyrano[3,2-c]quinolin-5(6H)-one 
• 106058-76-8 3,3'-((4-chlorophenyl)methylene)bis(4-hydroxy-1-methylquinolin-2(1H)-one) 
• 1438417-99-2 6-methyl-2-(methylamino)-3-nitro-4-p-tolyl-4H-pyrano[3,2-c]quinolin-5(6H)-one 

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