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Dimethylformamide → HCID 53748727, compound

HRID 437712
Notes
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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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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

  • stirringInto the mixture was stirred
  • customan exothermic reaction
  • concentrationThe mixture was concentrated under reduced pressure
  • customthe residue was recrystallized from ethanol
  • Sources & evidence

    ORD record
    ord-f2e3cd44ec96400ebcb60793fac6d257
    Source dataset
    uspto-grants-1977_06
    DOI
    10.6084/m9.figshare.5104873.v1
    Patent number
    US04032322

    Reaction notes

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    On this pageParticipantsProcedureWorkupSources & evidenceReaction notes