Water → HCID 20377184, compound

HRID 2052202Notes

Reaction equation

HRID 2052202 reaction equation
[CH3:1][N:2]([CH3:6])[C:3](Cl)=[O:4].[Cl-].[Al+3].[Cl-].[Cl-].[NH2:11][C:12]1[CH:16]=[C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[S:14][N:13]=1.O>C1(C)C=CC=CC=1>[CH3:1][N:2]([CH3:6])[C:3]([NH:11][C:12]1[CH:16]=[C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[S:14][N:13]=1)=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 6598Dimethylcarbamoyl ChlorideHCID 6451240Aluminum(III) ChlorideHCID 21271867HCID 21271867, compound

Product 1

HCID 20377184HCID 20377184, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

N,N-Dimethylcarbamoyl chloride (1.29 g) and aluminum chloride (1.60 g) are dissolved in toluene (40 ml), and the mixture is stirred at room temperature for 30 minutes. To this mixture is added 3-amino-5-phenylisothiazole (1.76 g), and the resulting mixture is refluxed for 6 hours with stirring. After cooling, the reaction mixture is mixed with water and shaken with toluene. The organic layer is separated, washed with water, dried, and concentrated to dryness to give 1,1-dimethyl-3-(5-phenyl-3-isothiazolyl)urea (2.38 g). Yield is 96.4%. Melting point of the colorless crystals is 129 to 130.5° C. (after recrystallization from benzene/petroleum benzin).

Workup

  1. temperaturethe resulting mixture is refluxed for 6 hours
  2. stirringwith stirring
  3. temperatureAfter cooling
  4. customThe organic layer is separated
  5. washwashed with water
  6. customdried
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-07a9120097bf4fc4ba28009e6b53f77b
Source dataset
uspto-grants-1980_01
Patent number
US04183856

Reaction notes

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