3-(Trifluoromethyl)phenyl isocyanate → HCID 67523894, compound

HRID 659035Notes

Reaction equation

HRID 659035 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[C:5]([N:9]=[C:10]=[O:11])[CH:6]=[CH:7][CH:8]=1.[CH3:14][S:15][C:16]1[N:21]=[C:20]([O:22][C:23]2[CH:28]=[CH:27][C:26]([NH2:29])=[CH:25][CH:24]=2)[CH:19]=[CH:18][N:17]=1>ClCCl>[CH3:14][S:15][C:16]1[N:21]=[C:20]([O:22][C:23]2[CH:28]=[CH:27][C:26]([NH:29][C:10]([NH:9][C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:12])([F:13])[F:1])[CH:4]=3)=[O:11])=[CH:25][CH:24]=2)[CH:19]=[CH:18][N:17]=1

Participants

4

Reactant 2

HCID 94833-(Trifluoromethyl)phenyl isocyanateHCID 67523926HCID 67523926, compound

Product 1

HCID 67523894HCID 67523894, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 41.7 g (219 mmol) 3-trifluoromethyl-phenyl isocyanate in 50 ml dichloromethane was added within 45 min. drop by drop at 5-10° C. to a solution of 51.0 g (219 mmol) 4-(2-Methylsulfanyl-pyrimidin-4-yloxy)-phenylamine and stirring continued for 5 h at 5° C. The reaction mixture was kept in a cooling room overnight at 4° C. The formed precipitate was isolated by cold filtration and washed thrice with 40 ml ice cold dichloromethane. After an additional washing with portions of isohexane (250 ml total) the product was dried at 40° C. in vacuum to give 73.4 g (80%) 1-[4-(2-methylsulfanyl-pyrimidin-4-yloxy)-phenyl]-3-(3-trifluoromethyl-phenyl)-urea.

Workup

  1. customwas kept in a cooling room overnight at 4° C
  2. customThe formed precipitate was isolated by cold filtration
  3. washwashed thrice with 40 ml ice cold dichloromethane
  4. washAfter an additional washing with portions of isohexane (250 ml total) the product
  5. customwas dried at 40° C. in vacuum

Sources & evidence

ORD record
ord-ff8605170f634133b103e46893d06965
Source dataset
uspto-grants-2011_12
Patent number
US08080552B2

Reaction notes

Loading…