Allyl chloride → HCID 15860210, compound

HRID 1419787Notes

Reaction equation

HRID 1419787 reaction equation
[CH2:1](Cl)[CH:2]=[CH2:3].[CH:5]1([O:10][C:11]2[CH:12]=[C:13]([CH2:19][C:20]([NH:22][C:23]3[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:24]=3[OH:30])=[O:21])[CH:14]=[CH:15][C:16]=2[O:17][CH3:18])[CH2:9][CH2:8][CH2:7][CH2:6]1>C(O)C.[OH-].[Na+].CO.O>[CH:5]1([O:10][C:11]2[CH:12]=[C:13]([CH2:19][C:20]([NH:22][C:23]3[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:24]=3[O:30][CH2:3][CH:2]=[CH2:1])=[O:21])[CH:14]=[CH:15][C:16]=2[O:17][CH3:18])[CH2:9][CH2:8][CH2:7][CH2:6]1

Participants

7

Reactant 2

HCID 7850Allyl chlorideHCID 15907399HCID 15907399, compound

Product 1

HCID 15860210HCID 15860210, compoundYield 65%

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

In this step, allyl chloride (23.3 grams, 0.31 mol) was added to a stirred solution of N-(3-cyclopentyloxy-4-methoxy-phenylacetyl)-2-hydroxy-5-chloroaniline (78 grams, 0.21 mol) in ethanol (600 millilters) and 1N NaOH in methanol (213 milliters). The mixture was heated under reflux for 8 hours and then diluted with water and extracted twice with ethyl acetate. Evaporation of the ethyl acetate and crystallization of the residue from methanol gave 56.4 grams (65%) of the title compound, mp 75-76.5°.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 8 hours
  3. extractionextracted twice with ethyl acetate
  4. customEvaporation of the ethyl acetate and crystallization of the residue from methanol

Sources & evidence

ORD record
ord-8108d934e0754a2db3c5fb6b3c70756b
Source dataset
uspto-grants-1999_03
Patent number
US05889014

Reaction notes

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