Dimethylformamide → HCID 20367597, compound

HRID 616495Notes

Reaction equation

HRID 616495 reaction equation
[C:1]([C:3]1[C:4]([N:18]([CH3:20])[CH3:19])=[N:5][S:6][C:7]=1[NH:8][C:9](=[O:17])OC1C=CC=CC=1)#[N:2].[CH3:21][N:22](C)[CH:23]=O>>[CH3:21][N:22]([CH3:23])[C:9]([NH:8][C:7]1[S:6][N:5]=[C:4]([N:18]([CH3:20])[CH3:19])[C:3]=1[C:1]#[N:2])=[O:17]

Participants

3

Reactant 2

HCID 6228DimethylformamideHCID 54004448HCID 54004448, compound

Product 1

HCID 20367597HCID 20367597, compound

Procedure

In a pressure bottle were placed 6.1 g of phenyl (4-cyano-3-(dimethylamino)-5-isothiazolyl)carbamate and 25 ml of dimethylformamide. This solution was cooled to 0°, and 2.8 ml (1.9 g) of dimethylamine (previously collected in a graduated dropping funnel using a dry-ice trap) were added. The reaction mixture was heated at 80° for 4 hours, cooled to -10° and the bottle was opened. The reaction mixture was concentrated to dryness under vacuum to give a tan solid. Recrystallization of the tan solid from ethanol gave 4.0 g of 1,1-dimethyl-3-(4-cyano-3-(dimethylamino)-5-isothiazolyl)urea, m.p. 203°-204°. A second crop was collected and was recrystallized from ethanol to give 0.2 g of needles; m.p. 201°-202°. The nmr spectrum was consistent with the assigned structure.

Workup

  1. temperatureThis solution was cooled to 0°
  2. custom2.8 ml (1.9 g) of dimethylamine (previously collected in
  3. additionwere added
  4. temperatureThe reaction mixture was heated at 80° for 4 hours
  5. temperaturecooled to -10°
  6. concentrationThe reaction mixture was concentrated to dryness under vacuum
  7. customto give a tan solid
  8. customRecrystallization of the tan solid from ethanol

Sources & evidence

ORD record
ord-bb937c0babe44f68a3b0c315236b6515
Source dataset
uspto-grants-1978_02
Patent number
US04075001

Reaction notes

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