Hydrochloric Acid → HCID 20489855, compound

HRID 1701180Notes

Reaction equation

HRID 1701180 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 temperature 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-63524c6d042b45f0a959b571a658f3e8
Source dataset
uspto-grants-1980_03
Patent number
US04191770

Reaction notes

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