Dimethylformamide → HCID 54093114, compound

HRID 616515Notes

Reaction equation

HRID 616515 reaction equation
[C:1]([C:3]1[C:4]([N:18]([CH2:20][CH3:21])[CH3:19])=[N:5][S:6][C:7]=1[NH:8][C:9](=[O:17])OC1C=CC=CC=1)#[N:2].[CH3:22][N:23](C)[CH:24]=O>>[CH3:22][N:23]([CH3:24])[C:9]([NH:8][C:7]1[S:6][N:5]=[C:4]([N:18]([CH2:20][CH3:21])[CH3:19])[C:3]=1[C:1]#[N:2])=[O:17]

Participants

3

Reactant 2

HCID 6228DimethylformamideHCID 54172873HCID 54172873, compound

Product 1

HCID 54093114HCID 54093114, compound

Procedure

A solution of 10.6 g of phenyl (4-cyano-3-(ethylmethylamino)-5-isothiazolyl)carbamate and 25 ml of dimethylformamide was placed in a pressure bottle. This solution was cooled and 5 ml of dimethylamine (previously collected in a dry-ice trap) were added. The pressure bottle was sealed and allowed to warm slowly to room temperature. The reaction mixture was then heated at 80° for approximately 16 hours. The reaction mixture was cooled in a dry ice bath and the vessel was opened. The reaction mixture was concentrated under reduced pressure until a small amount of material crystallized. Collection of the crystals produced 2.3 g of 1,1-dimethyl-3-(4-cyano-3-(ethylmethylamino)-5-isothiazolyl)urea, mp 115°-130° (decomposes). The ir and nmr spectra were consistent with the assigned structure.

Workup

  1. temperatureThis solution was cooled
  2. custom5 ml of dimethylamine (previously collected in a dry-ice trap)
  3. additionwere added
  4. customThe pressure bottle was sealed
  5. temperatureThe reaction mixture was then heated at 80° for approximately 16 hours
  6. temperatureThe reaction mixture was cooled in a dry ice bath
  7. concentrationThe reaction mixture was concentrated under reduced pressure until a small amount of material
  8. customcrystallized
  9. customCollection of the crystals

Sources & evidence

ORD record
ord-a1ba9d208e3340ed94748f3b99918dd6
Source dataset
uspto-grants-1978_02
Patent number
US04075001

Reaction notes

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