Bromoacetic Acid → 2-bromo-N-(2,6-dimethylphenyl)acetamide

HRID 1796893Notes

Reaction equation

HRID 1796893 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:3]=1[NH2:4].[Br:10][CH2:11][C:12](O)=[O:13]>C(Cl)Cl>[Br:10][CH2:11][C:12]([NH:4][C:3]1[C:5]([CH3:9])=[CH:6][CH:7]=[CH:8][C:2]=1[CH3:1])=[O:13]

Participants

4

Reactant 2

HCID 6227Bromoacetic AcidHCID 68962,6-Dimethylaniline

Product 1

HCID 27634872-bromo-N-(2,6-dimethylphenyl)acetamideYield 112.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

See FIG. 2, Formula T2. 8.1 Preparation of 2-bromo-N-(2, 60-dimethylphenyl)acetamide DCC (14.5 g; 70 mmol) was added to a cold solution of 2,6-dimethylaniline (8.5 g; 70 mmol) and bromoacetic acid (9.75 g; 70 mmol) in dry CH2Cl2 (400 mL) in portions over 30 min. The mixture was allowed to warm to room temperature overnight with stirring. It was then filtered, and the filtrate evaporated to dryness. The residual solid was dissolved in EtOAc (200 mL) and CH2C2 (200 mL). The mixture was filtered, and the filtrate evaporated to dryness to yield 2-bromo-N-(2,6-dimethylphenyl)acetamide (19 g). 8.2 Preparation of 1-(2,6-dimethylphenyl)-2,8,8-trioxo-1,4-diaza-7,8-dithianonane

Workup

  1. filtrationIt was then filtered
  2. customthe filtrate evaporated to dryness
  3. dissolutionThe residual solid was dissolved in EtOAc (200 mL)
  4. filtrationThe mixture was filtered
  5. customthe filtrate evaporated to dryness

Sources & evidence

ORD record
ord-c506a1b0360d46a18ad7159741f0f27b
Source dataset
uspto-grants-2006_04
Patent number
US07033765B1

Reaction notes

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