Dimethylformamide → HCID 53748727, compound

HRID 437712Notes

Reaction equation

HRID 437712 reaction equation
CS(Cl)(=O)=O.[NH2:6][C:7]1[S:11][N:10]=[C:9]([O:12][CH2:13][CH2:14][CH3:15])[C:8]=1[C:16]#[N:17].[CH3:18][N:19]([CH3:22])[CH:20]=O>>[C:16]([C:8]1[C:9]([O:12][CH2:13][CH2:14][CH3:15])=[N:10][S:11][C:7]=1[N:6]=[CH:18][N:19]([CH3:22])[CH3:20])#[N:17]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 31297Methanesulfonyl chlorideHCID 21396807HCID 21396807, compound

Product 1

HCID 53748727HCID 53748727, compound

Procedure

A mixture of 13.7 g of methanesulfonyl chloride in 25 ml of dimethylformamide was stirred at room temperature for about 16 hours. Into the mixture was stirred 11 g of 5-amino-4-cyano-3-propoxyisothiazole which addition caused an exothermic reaction. The mixture was concentrated under reduced pressure and the residue was recrystallized from ethanol to give 2.7 g of crystalline N'-(4-cyano-3-propoxy-5-isothiazolyl)-N,N-dimethylformamidine, m.p. 117°-118°. The nmr spectrum was consistent with the assigned structure.

Workup

  1. stirringInto the mixture was stirred
  2. customan exothermic reaction
  3. concentrationThe mixture was concentrated under reduced pressure
  4. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-f2e3cd44ec96400ebcb60793fac6d257
Source dataset
uspto-grants-1977_06
Patent number
US04032322

Reaction notes

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