Water → HCID 11771561, compound

HRID 1994283Notes

Reaction equation

HRID 1994283 reaction equation
[NH2:1][C:2]1[C:3]([CH3:13])=[CH:4][C:5]([Br:12])=[C:6]([CH:11]=1)[C:7]([NH:9][CH3:10])=[O:8].CCN(C(C)C)C(C)C.[Cl:23][CH2:24][C:25](Cl)=[O:26].O>CC(C)=O>[Br:12][C:5]1[CH:4]=[C:3]([CH3:13])[C:2]([NH:1][C:25](=[O:26])[CH2:24][Cl:23])=[CH:11][C:6]=1[C:7]([NH:9][CH3:10])=[O:8]

Participants

6

Reactant 4

HCID 962WaterHCID 6577Chloroacetyl chloride2×HCID 81531DiisopropylethylamineHCID 58786276HCID 58786276, compound

Product 1

HCID 11771561HCID 11771561, compoundYield 85.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 5-amino-2-bromo-N, 4-dimethylbenzamide (3A) (94 mg, 0.38 mmol) in acetone (4 mL) at 0° C. was added DIPEA (68 μL, 0.39 mmol) followed by 2-chloroacetylchloride (31 μL, 0.39 mmol). The solution was stirred for 60 minutes and another aliquot of 2-chloroacetylchloride (4 μL) was added. Water was added (94 mL) and the acetone removed in vacuo. The solids were stirred rapidly for 1 h, filtered and washed with water to give 104 mg (84% yield) of 2-bromo-5-(2-chloroacetamido)-N-methyl-4-methylbenzamide, 1H NMR: (CDCl3, 400 MHz) δ 8.28 (s, 1H), 8.03 (s, 1H), 7.44 (s, 1H), 6.01 (br s, 1H), 4.23 (s, 2H), 3.01 (d, J=5.0 Hz, 3H), 2.17 (s, 3H); LCMS 320.99 (M+H).

Workup

  1. customthe acetone removed in vacuo
  2. stirringThe solids were stirred rapidly for 1 h
  3. filtrationfiltered
  4. washwashed with water

Sources & evidence

ORD record
ord-27c280373c5d446da05498ca7b73bffc
Source dataset
uspto-grants-2010_01
Patent number
US07652146B2

Reaction notes

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