Phenacyl bromide → HCID 11405382, compound

HRID 1993800Notes

Reaction equation

HRID 1993800 reaction equation
[CH:1]1([NH:4][C:5](=[O:17])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([NH:13][C:14]([NH2:16])=[S:15])[CH:7]=2)[CH2:3][CH2:2]1.Br[CH2:19][C:20]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=O>C(O)C>[CH:1]1([NH:4][C:5](=[O:17])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([NH:13][C:14]3[S:15][CH:19]=[C:20]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[N:16]=3)[CH:7]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6259Phenacyl bromideHCID 86595436HCID 86595436, compound

Product 1

HCID 11405382HCID 11405382, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

To a stirred solution of N-Cyclopropyl-4-methyl-3-thioureido-benzamide 3A (41 mg, 0.16 mmol) in 5 mL of ethanol was added 2-bromoacetophenone (33 mg, 0.16 mmol) and the reaction was heated at 75° C. overnight. After 16 hours, the reaction was cooled and concentrated and the crude product was purified by flash chromatography on silica gel loaded with CH2Cl2 and eluted with 2:1 hexanes/ethyl acetate followed by 1:2 hexanes/ethyl acetate to provide the title compound as a solid (32 mg, 94%). HPLC, tR, 3.54 min.(6 minute method); MS, m/z 350.0 [M+1]+.

Workup

  1. temperaturethe reaction was cooled
  2. concentrationconcentrated
  3. customthe crude product was purified by flash chromatography on silica gel
  4. washeluted with 2:1 hexanes/ethyl acetate

Sources & evidence

ORD record
ord-9663fd3bde164e34aa4a3c6e18c149c2
Source dataset
uspto-grants-2010_01
Patent number
US07652044B2

Reaction notes

Loading…