Hydrochloric Acid → HCID 20489855, compound

HRID 1995187Notes

Reaction equation

HRID 1995187 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[C:6](Cl)=[O:7].C1(C2[NH:24][CH2:23][CH:22]([CH2:25][Cl:26])[O:21]2)C=CC=CC=1.Cl>C(Cl)(Cl)Cl.N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[C:6]([NH:24][CH2:23][CH:22]([OH:21])[CH2:25][Cl:26])=[O:7]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 77070Veratroyl chlorideHCID 2707015-(chloromethyl)-2-phenyl-1,3-oxazolidine

Product 1

HCID 20489855HCID 20489855, compoundYield 72.3%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6212ChloroformSolvent2×

Procedure

A solution of 15.2 g of 3,4-dimethoxybenzoyl chloride in 40 ml of chloroform is added dropwise to a solution of 15.0 g 2-phenyl-5-chloromethyloxazolidine in a mixture of 200 ml of chloroform and 6 ml of pyridine at a temperture of -40° C. under agitation. This solution is then heated to room temperature. After a reaction period of 14 hours, 20 ml of concentrated hydrochloric acid are added, the phases are thoroughly mixed for a period of 10 minutes and then are separated. The separated aqueous phase is diluted with water to twice its volume and then is saturated with sodium chloride and extracted with chloroform. After drying the chloroform-extract and evaporating the solvent, 15.0 g of N-(3,4-dimethoxybenzoyl)-3-chloro-1-aminopropan-2-ol is obtained as an oil which can be further reacted without any purification. After crystallization from ethanol/toluene the compound exhibits a melting point of 104°-106° C.

Workup

  1. additionare added
  2. additionthe phases are thoroughly mixed for a period of 10 minutes
  3. customare separated
  4. additionThe separated aqueous phase is diluted with water to twice its volume
  5. extractionextracted with chloroform
  6. dry with materialAfter drying the chloroform-
  7. extractionextract
  8. customevaporating the solvent

Sources & evidence

ORD record
ord-c0a5493d13834cb1b167c1cf30a93e98
Source dataset
uspto-grants-1983_09
Patent number
US04402981

Reaction notes

Loading…