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

HRID 224635

Reaction equation

HRID 224635 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-0168655c41f94fc4b8df7f4e22af38e2
Source dataset
uspto-grants-1980_11
Patent number
US04233302

Linked notes

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