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

HRID 1278008Notes

Reaction equation

HRID 1278008 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-baa6ac80ffa54a3f8ed41ae54e50705d
Source dataset
uspto-grants-1981_07
Patent number
US04279911

Reaction notes

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