Dimethylformamide → HCID 54385684, compound

HRID 2231959Notes

Reaction equation

HRID 2231959 reaction equation
O=P(Cl)(Cl)Cl.[NH2:6][C:7]1[S:11][N:10]=[C:9]([C:12]([NH2:14])=O)[C:8]=1[C:15]([NH2:17])=O.[CH3:18][N:19]([CH3:22])[CH:20]=O>>[CH3:18][N:19]([CH3:22])[CH:20]=[N:6][C:7]1[S:11][N:10]=[C:9]([C:12]#[N:14])[C:8]=1[C:15]#[N:17]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 21285250HCID 21285250, compound

Product 1

HCID 54385684HCID 54385684, compoundYield 93%

Procedure

10.1 parts of phosphorus oxytrichloride are added dropwise to 30 parts of dimethylformamide at 0° C., and the mixture is then stirred for a further 0.5 hour at this temperature. 3.7 parts of 5-aminoisothiazole-3,4-dicarboxamide are then introduced, a little at a time, into this solution while cooling with ice. The mixture is stirred for a further 2 hours at room temperature, after which it is poured into 100 parts of ice water. The precipitate is filtered off under suction, washed with water and dried to give 3.8 parts (93% of theory) of N,N-dimethyl-N'-(3,4-dicyanoisothiazol-5-yl)-formamidine.

Workup

  1. temperaturea little at a time, into this solution while cooling with ice
  2. stirringThe mixture is stirred for a further 2 hours at room temperature
  3. filtrationThe precipitate is filtered off under suction
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-d95fc5374a504742a1142f2c6328272c
Source dataset
uspto-grants-1988_11
Patent number
US04785116

Reaction notes

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