Oxalic Acid → N,N-Dimethyl-5-[[[2-[(1-methylthio-2-nitroethenyl)amino]ethyl]thio]methyl]-2-furanmethanamine oxalate

HRID 1277990Notes

Reaction equation

HRID 1277990 reaction equation
CS[CH:3]([S:8][CH3:9])[CH2:4][N+:5]([O-:7])=[O:6].[NH2:10][CH2:11][CH2:12][S:13][CH2:14][C:15]1[O:19][C:18]([CH2:20][N:21]([CH3:23])[CH3:22])=[CH:17][CH:16]=1.[C:24]([OH:29])(=[O:28])[C:25]([OH:27])=[O:26]>O1CCOCC1>[C:24]([OH:29])(=[O:28])[C:25]([OH:27])=[O:26].[CH3:22][N:21]([CH3:23])[CH2:20][C:18]1[O:19][C:15]([CH2:14][S:13][CH2:12][CH2:11][NH:10][C:3]([S:8][CH3:9])=[CH:4][N+:5]([O-:7])=[O:6])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 971Oxalic AcidHCID 1622035-(((2-Aminoethyl)thio)methyl)-N,N-dimethyl-2-furanmethanamineHCID 123722641,1-Bis(methylsulfanyl)-2-nitroethane

Product 1

HCID 70539027N,N-Dimethyl-5-[[[2-[(1-methylthio-2-nitroethenyl)amino]ethyl]thio]methyl]-2-furanmethanamine oxalateYield 99.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 1,1-bis(methylthio)-2-nitroethane (19.8 g) and 5-[[(2-aminoethyl)thio]methyl]-N,N-dimethyl-2-furanmethanamine (6.42 g) in dry dioxan (120 ml) was heated at 80° C. for 6 hours. Oxalic acid (3.8 g) in dry dioxan (40 ml) was added and the crystalline solid which separated was filtered, washed with dioxan and dried to give the title compound (12.55 g) m.p. 140°-143° C.

Workup

  1. customthe crystalline solid which separated
  2. filtrationwas filtered
  3. washwashed with dioxan
  4. customdried

Sources & evidence

ORD record
ord-9f864dffe3924553b53db590a22afe22
Source dataset
uspto-grants-1981_07
Patent number
US04279911

Reaction notes

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