3-(Trifluoromethyl)phenyl isocyanate → HCID 135500083, compound

HRID 2111965Notes

Reaction equation

HRID 2111965 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[NH:13][C:12](=[O:14])[O:11][N:10]=1.[F:15][C:16]([F:27])([F:26])[C:17]1[CH:18]=[C:19]([N:23]=[C:24]=[O:25])[CH:20]=[CH:21][CH:22]=1>C1COCC1>[Cl:8][C:6]1[CH:5]=[CH:4][C:3]([C:9]2[NH:13][C:12](=[O:14])[O:11][N:10]=2)=[C:2]([NH:1][C:24]([NH:23][C:19]2[CH:20]=[CH:21][CH:22]=[C:17]([C:16]([F:15])([F:26])[F:27])[CH:18]=2)=[O:25])[CH:7]=1

Participants

4

Reactant 2

HCID 94833-(Trifluoromethyl)phenyl isocyanateHCID 1360346823-(2-Amino-4-chlorophenyl)-1,2,4-oxadiazol-5(2H)-one

Product 1

HCID 135500083HCID 135500083, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-(2-Amino-4-chloro-phenyl)-4H-[1,2,4]oxadiazol-5-one (400 mg, 1.92 mmol) was dissolved in 20 ml dry THF and 3-trifluoromethyl-phenyl-isocyanate (450 mg, 2.40 mmol) was added and the reaction stirred for 16 hours. The solvent was reduced under vacuum and the product recrystallised from ethyl acetate and heptane to yield 480 mg (63%) of off-white crystalline solid (m.p. 246-248; decomposition).

Workup

  1. customthe product recrystallised from ethyl acetate and heptane

Sources & evidence

ORD record
ord-06d71198e0ec4e3da5527ee67b1bc718
Source dataset
uspto-grants-2009_04
Patent number
US07521480B2

Reaction notes

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