Benzhydrylamine → 2-Bromo-N-(diphenylmethyl)acetamide

HRID 2370923Notes

Reaction equation

HRID 2370923 reaction equation
[Br:1][CH2:2][C:3](Br)=[O:4].C(N(CC)CC)C.[CH:13]([NH2:26])([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>>[CH:13]([NH:26][C:3](=[O:4])[CH2:2][Br:1])([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 3

HCID 7036BenzhydrylamineHCID 8471TriethylamineHCID 61147Bromoacetyl bromide

Product 1

HCID 141859482-Bromo-N-(diphenylmethyl)acetamideYield 19.4%

Procedure

A solution of 2.91 g (14.39 mmol) of bromoacetyl bromide in 40 ml was cooled to 0° C. and 2.1 ml (14.39 mmol) of triethylamine and 2.64 g (14.39 mmol) of benzhydrylamine were successively added. The reaction solution was then evaporated to dryness under reduced pressure, and the resulting residue was purified on silica gel with EA as mobile phase. The product crystallized from the product fractions was filtered off with suction, washed with a little cold diethyl ether and dried under reduced pressure, resulting in 0.85 g of the title compound.

Workup

  1. customThe reaction solution was then evaporated to dryness under reduced pressure
  2. customthe resulting residue was purified on silica gel with EA as mobile phase
  3. customThe product crystallized from the product fractions
  4. filtrationwas filtered off with suction
  5. washwashed with a little cold diethyl ether
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-9be0440c64284ba4861e43624e54de49
Source dataset
uspto-grants-2014_04
Patent number
US08710232B2

Reaction notes

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