Chloroacetyl chloride → N-(2-(4-bromophenyl)-2-hydroxyethyl)-2-chloroacetamide

HRID 338412Notes

Reaction equation

HRID 338412 reaction equation
[NH2:1][CH2:2][CH:3]([C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][CH:6]=1)[OH:4].[OH-].[Na+].[Cl:14][CH2:15][C:16](Cl)=[O:17]>C(Cl)Cl.O>[Br:11][C:8]1[CH:9]=[CH:10][C:5]([CH:3]([OH:4])[CH2:2][NH:1][C:16](=[O:17])[CH2:15][Cl:14])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 14798Sodium HydroxideHCID 137289422-Amino-1-(4-bromophenyl)-1-ethanol

Product 1

HCID 86698749N-(2-(4-bromophenyl)-2-hydroxyethyl)-2-chloroacetamideYield 76%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of compound 2-amino-1-(4-bromophenyl)ethanol (2.0 g, 10 mmol) in CH2Cl2 (40 mL) and water (40 mL) was added NaOH (0.48 g, 12 mmol) and chloroacetyl chloride (1.7 g, 15 mmol) at 0° C. After addition, the mixture was allowed to warm to room temperature and stirred for 6 hours. The layers were separated. The organic was washed with 3% HCl and saturated NaHCO3, dried over sodium sulfate, and concentrated to afford the title compound (2.0 g, 76% yield) as a yellow solid. 1H NMR: (400 MHz, CDCl3): δ 7.45 (d, 2H), 7.19 (d, 2H), 6.98 (br. s, 1H), 4.80 (m, 1H), 4.01 (s, 2H), 3.68 (m, 1H), 3.30 (m, 1H), 2.82 (br. s, 1H):

Workup

  1. additionAfter addition
  2. customThe layers were separated
  3. washThe organic was washed with 3% HCl and saturated NaHCO3
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c7be4b531aa14164820b73777cba8bb2
Source dataset
uspto-grants-2014_11
Patent number
US08889730B2

Reaction notes

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