Dimethylformamide → HCID 54317905, compound

HRID 2049026Notes

Reaction equation

HRID 2049026 reaction equation
P(Cl)(Cl)(Cl)=O.[NH2:6][C:7]1[S:8][C:9]([N+:14]([O-:16])=[O:15])=[CH:10][C:11]=1[C:12]#[N:13].[CH3:17][N:18]([CH3:21])[CH:19]=O>>[CH3:17][N:18]([CH:21]=[N:6][C:7]1[S:8][C:9]([N+:14]([O-:16])=[O:15])=[CH:10][C:11]=1[C:12]#[N:13])[CH3:19]

Participants

4

Reactant 3

HCID 6228Dimethylformamide2×HCID 24813Phosphorus oxychlorideHCID 110520602-AMINO-3-CYANO-5-NITROTHIOPHENE

Product 1

HCID 54317905HCID 54317905, compound

Procedure

Phosphorus oxychloride (5 ml) was added dropwise, with stirring, to dry N,N-dimethylformamide (20 ml) maintaining the temperature below 5° C. The solution was allowed to stand for fifteen minutes then treated, at 0°-5° C., with a suspension of 2-amino-3-cyano-5-nitrothiophene (5.1 g) in dry N,N-dimethylformamide (50 ml), allowed to attain room temperature, then kept at 20° C. for five days. It was then poured on to ice, the precipitate removed and the filtrate basified with ammonium hydroxide solution to give 2-dimethylaminomethyleneamino-3-cyano-5-nitrothiophene (m.p. 230°). A mixture of this material (0.5 g), benzylamine (0.26 g) and ethanol (100 ml) was refluxed for twelve hours, treated with acetic acid (0.5 ml) and heating continued for a further thirty minutes. The solvent was removed in vacuo and the residue diluted with water to give 4-benzylamino-6-nitrothieno[2,3-d]pyrimidine (0.4 g) (Compound No. 136).

Workup

  1. temperaturemaintaining the temperature below 5° C
  2. waitto stand for fifteen minutes
  3. customto attain room temperature
  4. additionIt was then poured on to ice
  5. customthe precipitate removed

Sources & evidence

ORD record
ord-93b3b85c9ba646e7a8caa91933d51187
Source dataset
uspto-grants-1980_04
Patent number
US04196207

Reaction notes

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