Water → (RS)-N-(4-Benzyloxy-phenyl)-2,4-dibromo-butyramide

HRID 1768126Notes

Reaction equation

HRID 1768126 reaction equation
[CH2:1]([O:8][C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[Br:23][CH:24]([CH2:28][CH2:29][Br:30])[C:25](Cl)=[O:26].O>ClCCl>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([NH:13][C:25](=[O:26])[CH:24]([Br:23])[CH2:28][CH2:29][Br:30])=[CH:14][CH:15]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 228604-BenzyloxyanilineHCID 44131432,4-Dibromobutyryl chloride

Product 1

HCID 23614762(RS)-N-(4-Benzyloxy-phenyl)-2,4-dibromo-butyramideYield 22.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 12.8 g (64.2 mmol) 4-benzyloxyaniline and 9.74 g (96.3 mmol) triethylamine in 125 ml dichloromethane is cooled to 0° C. 20.4 g (77.1 mmol) of 2,4-dibromobutyryl chloride [Ikuta et al., J. Med. Chem. 30:1995 (1987)] is slowly added over a period of 45 min. The reaction mixture is stirred for additional 15 min, then hydrolysed with 100 ml of water. The insoluble precipitate is filtered off and the organic phase is washed successively with a saturated solution of sodium hydrogencarbonate and water. After drying and evaporation, the crude product is subjected to chromatography (silica gel, dichloromethane) to yield 6.1 g (22%) of a colorless solid. Mp=139.5–142° C.

Workup

  1. filtrationThe insoluble precipitate is filtered off
  2. washthe organic phase is washed successively with a saturated solution of sodium hydrogencarbonate and water
  3. customAfter drying
  4. customevaporation

Sources & evidence

ORD record
ord-256f0b54b0f54f1f96eacf864eb6c106
Source dataset
uspto-grants-2007_06
Patent number
US07235581B2

Reaction notes

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