Isocyanate → 1-(2,6-Dichlorobenzoyl)-3-(5-(4-(trifluoromethyl)phenyl)-3-isoxazolyl)urea

HRID 1156525Notes

Reaction equation

HRID 1156525 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][N:12]=[C:11]([NH2:14])[CH:10]=2)=[CH:5][CH:4]=1.[Cl:17][C:18]1[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[C:19]=1[C:20]([N:22]=[C:23]=[O:24])=[O:21].[N-]=C=O>CO>[Cl:17][C:18]1[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[C:19]=1[C:20]([NH:22][C:23]([NH:14][C:11]1[CH:10]=[C:9]([C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:15])[F:16])=[CH:8][CH:7]=2)[O:13][N:12]=1)=[O:24])=[O:21]

Participants

5

Reactant 3

HCID 105034IsocyanateHCID 129127392,6-Dichlorobenzoyl isocyanateHCID 130355455-[4-(Trifluoromethyl)phenyl]-1,2-oxazol-3-amine

Product 1

HCID 129600431-(2,6-Dichlorobenzoyl)-3-(5-(4-(trifluoromethyl)phenyl)-3-isoxazolyl)urea

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-(4-(Trifluoromethyl)phenyl)-3-aminoisoxazole (500 grams) in 6 l. 1,2-dichloromethane was reacted in a reaction vessel with 2,6-dichlorobenzoyl isocyanate (567 grams). The isocyanate was added in rapid dropwise fashion over one hour keeping the temperature between 20°-40° C. The reaction mixture was allowed to react at 40° C. for three hours and was then stripped and slurried in 1 l. methanol. A white solid product formed which was filtered, dried in an air dryer, and then identified by NMR analysis as the desired compound, yield, 881 grams, m.p.=227°-230° C.

Workup

  1. custombetween 20°-40° C
  2. customto react at 40° C. for three hours
  3. customA white solid product formed which
  4. filtrationwas filtered
  5. customdried in an air dryer
  6. customyield

Sources & evidence

ORD record
ord-17240e3c489e43f18519349aa37c9f30
Source dataset
uspto-grants-1982_06
Patent number
US04336264

Reaction notes

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