Chloroacetyl chloride → HCID 21861287, compound

HRID 595971Notes

Reaction equation

HRID 595971 reaction equation
[NH2:1][C@@H:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:3][OH:4].CCN(CC)CC.[Cl:18][CH2:19][C:20](Cl)=[O:21]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Cl:18][CH2:19][C:20]([NH:1][C@@H:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:3][OH:4])=[O:21]

Participants

6

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 1347972-Amino-2-phenylethan-1-ol

Product 1

HCID 21861287HCID 21861287, compoundYield 45.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (S)-2-amino-2-phenylethanol (0.852 g, 6.21 mmol), Et3N (0.952 mL, 6.83 mmol), DMAP (76 mg, 0.621 mmol) in CH2Cl2 (10 mL) at 0° C. was added 2-chloroacetyl chloride (0519 mL, 6.52 mmol), and the resulting mixture was stirred at 0° C. for 15 min. The reaction mixture was washed with aqueous HCl (1 M, 20 mL), then sat. NaHCO3 (20 mL), dried (Na2SO4), concentrated, further dried under high vacuum and (S)-2-chloro-N-(2-hydroxy-1-phenylethyl)acetamide (0.60 g, 45.2% yield) was obtained as white solid. LCMS (m/z): 214 (MH+), 0.44 min.

Workup

  1. washThe reaction mixture was washed with aqueous HCl (1 M, 20 mL)
  2. dry with materialsat. NaHCO3 (20 mL), dried (Na2SO4)
  3. concentrationconcentrated
  4. customfurther dried under high vacuum

Sources & evidence

ORD record
ord-ccd66088b7794f4c8a79a7a891bcf704
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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