6-Aminobenzothiazole → (2E)-N-Benzothiazol-6-yl-3-[2-bromo-4-(trifluoromethyl)phenyl]prop-2-enamide

HRID 2105595Notes

Reaction equation

HRID 2105595 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1/[CH:12]=[CH:13]/[C:14]([OH:16])=O.[NH2:17][C:18]1[CH:26]=[CH:25][C:21]2[N:22]=[CH:23][S:24][C:20]=2[CH:19]=1>>[S:24]1[C:20]2[CH:19]=[C:18]([NH:17][C:14](=[O:16])/[CH:13]=[CH:12]/[C:3]3[CH:4]=[CH:5][C:6]([C:8]([F:9])([F:10])[F:11])=[CH:7][C:2]=3[Br:1])[CH:26]=[CH:25][C:21]=2[N:22]=[CH:23]1

Participants

3

Reactant 2

HCID 682886-AminobenzothiazoleHCID 578081432-Bromo-4-(trifluoromethyl)cinnamic acid

Product 1

HCID 57808138(2E)-N-Benzothiazol-6-yl-3-[2-bromo-4-(trifluoromethyl)phenyl]prop-2-enamide

Procedure

Analogous to the procedure used to prepare Example 1, (2E)-3-[2-bromo-4-(trifluoromethyl)phenyl]prop-2-enoic acid, Example 97(e), (140 mg, 0.47 mmol) and 6-aminobenzothiazole (86 mg, 0.57 mmol, Lancaster) provided, after purification by silica gel chromatography (gradient: 0-30% EtOAc in hexane), the title product as an off-white solid. MP 214-215° C. MS (ESI, pos. ion) m/z: 427 (M+1).

Workup

  1. customprovided
  2. customafter purification by silica gel chromatography (gradient: 0-30% EtOAc in hexane)

Sources & evidence

ORD record
ord-73df5304cd6f4d19a22eec65aae4e17e
Source dataset
uspto-grants-2009_08
Patent number
US07579347B2

Reaction notes

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