Ammonia → 2-[4-(Bromomethyl)phenyl]acetamide

HRID 1518202Notes

Reaction equation

HRID 1518202 reaction equation
[Br:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=O)=[CH:5][CH:4]=1.C[N:14](C)C=O.C1(C)C=CC=CC=1.N>O>[Br:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([NH2:14])=[O:12])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 1140TolueneHCID 6228DimethylformamideHCID 45190564-(Bromomethyl)phenylacetic acid

Product 1

HCID 179470252-[4-(Bromomethyl)phenyl]acetamideYield 393%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of (4-bromomethyl-phenyl)-acetic acid (9.23 g, 40.30 mmol) and N,N-dimethylformamide (0.5 ml, 6.47 mmol) in toluene (100 ml) thionyl chloride (3.1 ml, 42.31 mmol) was added. The mixture was heated at 80° C. for 1 h. At 0° C., this mixture was added to a solution of ammonia in water (25%, 200 ml). After stirring for 30 min the precipitate was collected, washed with water and pentane, and dried in a vacuum oven at 50° C. to give the product as white crystals (5.8 g, 63%).

Workup

  1. customwas collected
  2. washwashed with water and pentane
  3. customdried in a vacuum oven at 50° C.

Sources & evidence

ORD record
ord-c26bc974a13d412d938d8d9159f17198
Source dataset
uspto-grants-2012_07
Patent number
US08232426B2

Reaction notes

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