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

HRID 1659588Notes

Reaction equation

HRID 1659588 reaction equation
[CH3:1][NH:2][CH2:3][C:4]1[O:8][C:7]([CH2:9][S:10][CH2:11][CH2:12][NH2:13])=[CH:6][CH:5]=1.[CH3:14][S:15][C:16](SC)=[CH:17][N+:18]([O-:20])=[O:19].[C:23]([OH:28])(=[O:27])[C:24]([OH:26])=[O:25]>CN(C)C=O>[C:23]([OH:28])(=[O:27])[C:24]([OH:26])=[O:25].[CH3:1][NH:2][CH2:3][C:4]1[O:8][C:7]([CH2:9][S:10][CH2:11][CH2:12][NH:13][C:16]([S:15][CH3:14])=[CH:17][N+:18]([O-:20])=[O:19])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 971Oxalic AcidHCID 836231,1-Bis(methylthio)-2-nitroethyleneHCID 202094925-[[(2-Aminoethyl)thio]methyl]-N-methyl-2-furanmethanamine

Product 1

HCID 131711940N-Methyl-5-[[[2-[(1-methylthio-2-nitroethenyl) amino]ethyl]thio]methyl]-2-furanmethanamine, oxalate saltYield 26.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 2-[[5-[(methylamino)methyl]-2-furanylmethyl]thio]ethanamine (6.0 g) and 1,1-bis-(methylthio)-2-nitroethene (19.8 g) in dry dimethylformamide (150 ml) was stirred for 1 hour at 0° and for 5 hours at room temperature. A solution of oxalic acid (4.0 g) in dry dimethylformamide (16 ml) was added and the solid which formed during 18 hours was filtered, washed with dimethylformamide, ethanol and ether and dried. The solid was suspended in water (200 ml) at 55° and on cooling was filtered, washed with water and dried to give the title compound (3.25 g) m.p. 158°-160° dec.

Workup

  1. customthe solid which formed during 18 hours
  2. filtrationwas filtered
  3. washwashed with dimethylformamide, ethanol and ether
  4. customdried
  5. customwas suspended in water (200 ml) at 55°
  6. temperatureon cooling
  7. filtrationwas filtered
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-73c31c65660a4e7b97da63ede577be85
Source dataset
uspto-grants-1981_12
Patent number
US04304780

Reaction notes

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