Hydrochloric Acid → N-(3-Chloro-2-hydroxypropyl)acetamide

HRID 1995186Notes

Reaction equation

HRID 1995186 reaction equation
C(Cl)(=[O:3])C.[C:5]1([CH:11]2[NH:15][CH2:14][CH:13]([CH2:16][Cl:17])[O:12]2)C=CC=CC=1.Cl>C(Cl)(Cl)Cl.N1C=CC=CC=1>[C:11]([NH:15][CH2:14][CH:13]([OH:12])[CH2:16][Cl:17])(=[O:3])[CH3:5]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 2707015-(chloromethyl)-2-phenyl-1,3-oxazolidine

Product 1

HCID 11286567N-(3-Chloro-2-hydroxypropyl)acetamideYield 65%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6212ChloroformSolvent

Procedure

15.7 g of acetylchloride are added dropwise to a solution of 39.5 g of 2-phenyl-5-chloromethyloxazolidine in a mixture of 150 ml of chloroform and 16 ml of pyridine at a temperature of -40° C. under agitation. The solution is allowed to warm up to room temperature. After a reaction period of 14 hours, 100 ml of concentrated hydrochloric acid are added. After thoroughly mixing, the aqueous phase is separated and diluted with water to twice its volume and then is saturated with sodium chloride. By extracting the aqueous phase with methylene chloride, drying the methylene-chloride-extract and evaporating the solvent, 19.7 g of N-acetyl-3-chloro-1-aminopropan-2-ol is obtained as an oil which can be used in the following reaction without any purification.

Workup

  1. additionare added
  2. additionAfter thoroughly mixing
  3. customthe aqueous phase is separated
  4. additiondiluted with water to twice its volume
  5. extractionBy extracting the aqueous phase with methylene chloride
  6. dry with materialdrying the methylene-chloride-
  7. extractionextract
  8. customevaporating the solvent

Sources & evidence

ORD record
ord-3c51d1e9270246f0bdbb3be6d79df807
Source dataset
uspto-grants-1983_09
Patent number
US04402981

Reaction notes

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