4-(Trifluoromethyl)phenyl isocyanate → 4-[alpha-(2,4-Ditert.-pentylphenoxy)-butyroyl]-6-hydroxy-7-(4-trifluoromethylphenylureido)-1,4-benzoxazine-3-one

HRID 34705

Reaction equation

HRID 34705 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][C:6]([N:9]=[C:10]=[O:11])=[CH:5][CH:4]=1.[C:14]([C:19]1[CH:43]=[C:42]([C:44]([CH2:47][CH3:48])([CH3:46])[CH3:45])[CH:41]=[CH:40][C:20]=1[O:21][CH:22]([CH2:38][CH3:39])[C:23]([N:25]1[C:30]2[CH:31]=[C:32]([OH:36])[C:33]([NH2:35])=[CH:34][C:29]=2[O:28][CH2:27][C:26]1=[O:37])=[O:24])([CH2:17][CH3:18])([CH3:16])[CH3:15]>C1COCC1>[C:14]([C:19]1[CH:43]=[C:42]([C:44]([CH2:47][CH3:48])([CH3:45])[CH3:46])[CH:41]=[CH:40][C:20]=1[O:21][CH:22]([CH2:38][CH3:39])[C:23]([N:25]1[C:30]2[CH:31]=[C:32]([OH:36])[C:33]([NH:35][C:10]([NH:9][C:6]3[CH:5]=[CH:4][C:3]([C:2]([F:12])([F:13])[F:1])=[CH:8][CH:7]=3)=[O:11])=[CH:34][C:29]=2[O:28][CH2:27][C:26]1=[O:37])=[O:24])([CH2:17][CH3:18])([CH3:16])[CH3:15]

Participants

4

Reactant 2

HCID 737684-(Trifluoromethyl)phenyl isocyanateHCID 212986754-[alpha-(2,4-Ditert.-pentylphenoxy)-butyroyl]6-hydroxy-7-amino-1,4-benzoxazine-3-one

Product 1

HCID 867408204-[alpha-(2,4-Ditert.-pentylphenoxy)-butyroyl]-6-hydroxy-7-(4-trifluoromethylphenylureido)-1,4-benzoxazine-3-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Trifluoromethylphenylisocyanate (2.55 g, 0.0136 mole) was added to the amine ((g), 6.56 g, 0.0136 mole) in THF (ml 100). After 1 hour stirring, the solution was evaporated to dryness and the residue crystallized from toluene to give the coupler ((h), 6 g, 67%) as white prisms. The product structure was confirmed by NMR analysis.

Workup

  1. customthe solution was evaporated to dryness
  2. customthe residue crystallized from toluene

Sources & evidence

ORD record
ord-bdd15068de3742a7b850ca63c0514cab
Source dataset
uspto-grants-1988_08
Patent number
US04762925

Linked notes

Loading…