Cyclohexylpropionyl chloride → HCID 68712047, compound

HRID 1820128Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([C:11]([F:14])([F:13])[F:12])[C:3]=1[NH2:15].[CH:16]1([CH2:22][CH2:23][C:24](Cl)=[O:25])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1>C(#N)C>[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([C:11]([F:14])([F:13])[F:12])[C:3]=1[NH:15][C:24](=[O:25])[CH2:23][CH2:22][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

Conditions

Temperature: 150 °C

Procedure

2-Bromo-4-nitro-6-trifluoromethyl-phenylamine (2.0 g) and cyclohexylpropionyl chloride (1.30 mL) were mixed in acetonitrile (10 mL) and heated to 150° C. for 10 minutes in a sealed microwave process vial. The reaction was cooled to 0° C., the product filtered off and washed with cold acetonitrile (50 mL) affording 0.97 g (33% yield) of the title compound as a yellow solid. The crude product was used without further purification. LC-MS (m/z) 424 (MH+); tR=3.53, (UV, ELSD) 95%, 99%. 1H NMR (500 MHz, DMSO-d6): 0.88 (m, 2H), 1.17 (m, 3H), 1.28 (m, 1H), 1.51 (m, 2H), 1.68 (m, 5H), 2.38 (t, 2H), 8.45 (d, 1H), 8.82 (d, 1H), 10.17 (s, 1H).

Workup

temperatureThe reaction was cooled to 0° C.
filtrationthe product filtered off
washwashed with cold acetonitrile (50 mL)

Sources & evidence

ORD record: ord-b71213bd48a7486cbe1c3c592ceaa3e0
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07601870B2

Reaction notes

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