Oxalic acid dihydrate → N,N-dimethyl-3-[3-[(1-methylthio-2-nitroethenyl)amino]propoxy]benzenemethanamine

HRID 1277991Notes

Reaction equation

HRID 1277991 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH2:12][N:13]([CH3:15])[CH3:14])[CH:9]=[CH:10][CH:11]=1.[CH3:16][S:17][CH:18](SC)[CH2:19][N+:20]([O-:22])=[O:21].O.O.C(O)(=O)C(O)=O>O1CCCC1>[CH3:15][N:13]([CH3:14])[CH2:12][C:8]1[CH:9]=[CH:10][CH:11]=[C:6]([O:5][CH2:4][CH2:3][CH2:2][NH:1][C:18]([S:17][CH3:16])=[CH:19][N+:20]([O-:22])=[O:21])[CH:7]=1

Participants

5

Reactant 3

HCID 61373Oxalic acid dihydrateHCID 123722641,1-Bis(methylsulfanyl)-2-nitroethaneHCID 129139503-(3-Aminopropoxy)-N,N-dimethylbenzenemethanamine

Product 1

HCID 70538402N,N-dimethyl-3-[3-[(1-methylthio-2-nitroethenyl)amino]propoxy]benzenemethanamineYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-(3-Aminopropoxy)-N,N-dimethylbenzenemethanamine (10 g) and 1,1-bis-(methylthio)-2-nitroethane (16 g) were heated under reflux in tetrahydrofuran for 19 hours. Oxalic acid dihydrate (1.3 g) was added and the resulting precipitate was discarded. The solvent was removed to leave the title compound as a crystalline solid (10 g) m.p. 59°-63°.

Workup

  1. customThe solvent was removed

Sources & evidence

ORD record
ord-d0757245cef04b60bf0ef71df0862c9a
Source dataset
uspto-grants-1981_07
Patent number
US04279911

Reaction notes

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