Allyl chloride → HCID 15860210, compound

HRID 842083Notes

Reaction equation

HRID 842083 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH2:15][C:16]([NH:18][C:19]3[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:20]=3[OH:26])=[O:17])[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:27](Cl)[CH:28]=[CH2:29]>C(O)C.[OH-].[Na+].CO.O>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH2:15][C:16]([NH:18][C:19]3[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:20]=3[O:26][CH2:29][CH:28]=[CH2:27])=[O:17])[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]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

To a stirred solution of N-(3-cyclopentyloxy-4-methoxyphenylacetyl)-2-hydroxy-5-chloroaniline (78 g, 0.21 mol) in ethanol (600 ml) and 1 N NaOH in methanol (213 ml) was added allyl chloride (23.3 g, 0.31 mol). The mixture was heated under reflux for 8 hours, after which it was diluted with water and extracted twice with ethyl acetate. Evaporation of the ethyl acetate and crystallization of the residue from methanol gave 56.4 g (65%) of the title compound, mp 75-76.5° C.

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-0bcde7583ce948df83accef7081404cd
Source dataset
uspto-grants-2002_04
Patent number
US06372770B1

Reaction notes

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