Hydrochloric Acid → HCID 20489855, compound

HRID 1447643Notes

Reaction equation

HRID 1447643 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

At a temperature of -40° C., a solution of 15.2 g 3,4-dimethoxybenzoyl chloride in 40 ml of chloroform is added dropwise to a solution of 15.0 g of 2-phenyl-5-chloromethyloxazolidine in a mixture of 200 ml of chloroform and 6 ml of pyridine. The mixture is 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 10 minutes, and then separated. The separated aqueous phase is diluted with water to twice its volume and is saturated with sodium chloride. Then it is 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 used in the following reaction without any prior purification. After crystallization from ethanol/toluene, the compound melts at 104°-106° C.

Workup

  1. additionare added
  2. additionthe phases are thoroughly mixed for 10 minutes
  3. customseparated
  4. additionThe separated aqueous phase is diluted with water to twice its volume
  5. extractionThen it is extracted with chloroform
  6. dry with materialAfter drying the chloroform
  7. extractionextract
  8. customevaporating the solvent

Sources & evidence

ORD record
ord-b064941fb30345fd899bfcbda2f683e0
Source dataset
uspto-grants-1979_12
Patent number
US04177287

Reaction notes

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