4-Bromophenacyl bromide → HCID 86689666, compound

HRID 1622998Notes

Reaction equation

HRID 1622998 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13](=[S:15])[NH2:14])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].Br[CH2:19][C:20]([C:22]1[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][CH:23]=1)=O>C(O)(C)C>[Br:28][C:25]1[CH:26]=[CH:27][C:22]([C:20]2[N:14]=[C:13]([C:12]3[CH:16]=[CH:17][C:9]([O:8][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])=[CH:10][CH:11]=3)[S:15][CH:19]=2)=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 74544-Bromophenacyl bromideHCID 126805964-(Heptyloxy)benzothioamide

Product 1

HCID 86689666HCID 86689666, compoundYield 41.6%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a stirring mixture of 4-(heptyloxy)benzothioamide (1.30 g, 5.17 mmol) in isopropanol (20 mL) was added 2-bromo-1-(4-bromophenyl)ethanone (1.44 g, 5.17 mmol). The precipitate was collected by filtration and washed with EtOH (2×5 mL). The filter cake was slurried with NaHCO3 (2×20 mL), water (2×20 mL) then EtOH (2×5 mL) and dried to afford 926 mg (41%) of 4-(4-bromophenyl)-2-(4-(heptyloxy)phenyl)thiazole as a pale yellow powder. LCMS-ESI (m/z) calculated for C22H24BrNOS: 429.1; found 430.0 [M+H]+, tR=3.41 min. (Method 4).

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with EtOH (2×5 mL)
  3. dry with materialEtOH (2×5 mL) and dried

Sources & evidence

ORD record
ord-97b2fabaf58547e5bbfc17252b41f86e
Source dataset
uspto-grants-2014_07
Patent number
US08778923B2

Reaction notes

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