Triethylamine → (2-Methyl-6-trifluoromethylphenyl)isocyanate

HRID 1092328Notes

Reaction equation

HRID 1092328 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[C:3]=1[NH2:12].C12CC3CC(CC(C3)C1N=[C:24]=[O:25])C2.ClC(OC(=O)OC(Cl)(Cl)Cl)(Cl)Cl.C(N(CC)CC)C>C(Cl)Cl>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([F:9])([F:10])[F:11])[C:3]=1[N:12]=[C:24]=[O:25]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 128826302-IsocyanatoadamantaneHCID 133182332-Amino-3-methylbenzotrifluoride

Product 1

HCID 53750761(2-Methyl-6-trifluoromethylphenyl)isocyanate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

This compound was made from 2-methyl-6-trifluoromethyl-phenylamine in analogy to Eur. J. Med. Chem. 28 (1), 1993, 37-45 by treatment with bis-(trichloromethyl)-carbonate (627 mg) and triethylamine (1.58 mL) in DCM (16 mL). (2-Methyl-6-trifluoromethylphenyl)isocyanate was obtained as a colorless solid (1.17 g). 1H-NMR (δ, CDCl3): 7.49 (d, J=7.8 Hz, 1H), 7.41 (d, J=7.5 Hz, 1H), 7.20 (t, J=7.8 Hz, 1H), 2.40 (s, 3H).

Sources & evidence

ORD record
ord-3e9a823c240f4c32bd0d2297b3d66192
Source dataset
uspto-grants-2012_03
Patent number
US08129423B2

Reaction notes

Loading…