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

HRID 224649

Reaction equation

HRID 224649 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][CH:16](SC)[CH2:17][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 123722641,1-Bis(methylsulfanyl)-2-nitroethaneHCID 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-nitroethane (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-36f2bc0b14104a2596250c41c9eacbfe
Source dataset
uspto-grants-1980_11
Patent number
US04233302

Linked notes

Loading…