Hydrochloric Acid → 3-amino-N-[2,6-dibromo-4-(1,2,2,3,3,3-hexafluoro-1-trifluoromethylpropyl)-phenyl]-4-(1,2,4-triazol-1-yl)benzamide

HRID 1253405Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[C:6]([C:8]([F:20])([C:16]([F:19])([F:18])[F:17])[C:9]([F:15])([F:14])[C:10]([F:13])([F:12])[F:11])[CH:5]=[C:4]([Br:21])[C:3]=1[NH:22][C:23](=[O:38])[C:24]1[CH:29]=[CH:28][C:27]([N:30]2[CH:34]=[N:33][CH:32]=[N:31]2)=[C:26]([N+:35]([O-])=O)[CH:25]=1.Cl>C(O)C.O.[Fe]>[NH2:35][C:26]1[CH:25]=[C:24]([CH:29]=[CH:28][C:27]=1[N:30]1[CH:34]=[N:33][CH:32]=[N:31]1)[C:23]([NH:22][C:3]1[C:2]([Br:1])=[CH:7][C:6]([C:8]([F:20])([C:16]([F:17])([F:18])[F:19])[C:9]([F:14])([F:15])[C:10]([F:12])([F:13])[F:11])=[CH:5][C:4]=1[Br:21])=[O:38]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of N-[2,6-dibromo-4-(1,2,2,3,3,3-hexafluoro-1-trifluoromethylpropyl)-phenyl]-3-nitro-4-(1,2,4-triazol-1-yl)benzamide (Example I2) (675 mg, 0.98 mmol) in a mixture of ethanol and water (20 ml and 4 ml, respectively) was added aqueous hydrochloric acid (37% w/v) (0.25 ml) and iron metal powder (5550 mg, 9.8 mmol). The reaction mixture was stirred at 80° C. for 1 hour. The mixture was filtered through a silica gel pad and the filtrate concentrated. The residue was purified by column chromatography on silica gel (eluent: cyclohexane/ethyl acetate 1:1) to give Compound No. B4 of Table B (372 mg, 58% yield).

Workup

filtrationThe mixture was filtered through a silica gel pad
concentrationthe filtrate concentrated
customThe residue was purified by column chromatography on silica gel (eluent: cyclohexane/ethyl acetate 1:1)
customto give Compound No

Sources & evidence

ORD record: ord-c179d40fa169447a94da9c4f096b6e52
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08455399B2

Reaction notes

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