Water → HCID 68697913, compound

HRID 2244388Notes

Reaction equation

HRID 2244388 reaction equation
[NH2:1][C:2]1[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][C:3]=1[C:4]([N:6]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]([CH3:29])([CH3:28])[CH3:27])=[CH:22][CH:21]=1)[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=1)=[O:5].[Br:35]N1C(=O)CCC1=O.O.C(Cl)Cl>C(#N)C>[NH2:1][C:2]1[C:33]([Br:35])=[CH:32][C:31]([CH3:34])=[CH:30][C:3]=1[C:4]([N:6]([CH2:19][C:20]1[CH:21]=[CH:22][C:23]([C:26]([CH3:29])([CH3:28])[CH3:27])=[CH:24][CH:25]=1)[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:16])([F:17])[F:18])[CH:10]=1)=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 67184N-bromobutanimideHCID 68699037HCID 68699037, compound

Product 1

HCID 68697913HCID 68697913, compoundYield 71.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
75 °C

Procedure

2-Amino-N-(4-tert-butyl-benzyl)-5-methyl-N-[2-(3-trifluoromethyl-phenyl)-ethyl]-benzamide (60 mg, 0.128 mmol) was dissolved in acetonitrile (2 ml) and N-bromosuccinimide (23 mg, 0.128 mmol) was added. The reaction was heated to 75° C. for 4 h. The reaction mixture was cooled to RT and partitionated between water and methylene chloride. The aqueous layer was extracted with methylene chloride and the combined organic phase was dried (MgSO4), filtered and concentrated in vacuo to give the desired product (50 mg, 71%) as a light brown oil. MS (ISP) 547.3 (M+H)+.

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. extractionThe aqueous layer was extracted with methylene chloride
  3. dry with materialthe combined organic phase was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f6a8f84961c048939ca867c8ae4510b6
Source dataset
uspto-grants-2010_03
Patent number
US07678818B2

Reaction notes

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