Boron trifluoride etherate → N-(2-chlorobenzyl)-3-methoxyphenylacetamide

HRID 1731837Notes

Reaction equation

HRID 1731837 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][C:10]([OH:12])=O)[CH:6]=[CH:7][CH:8]=1.[Cl:13][C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[CH2:16][NH2:17].C(N(CC)CC)C.B(F)(F)F.CCOCC>C1(C)C=CC=CC=1>[Cl:13][C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[CH2:16][NH:17][C:10](=[O:12])[CH2:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1

Participants

6

Reactant 4

HCID 8000Boron trifluoride etherateHCID 8471TriethylamineHCID 15719(3-Methoxyphenyl)acetic acidHCID 666482-Chlorobenzylamine

Product 1

HCID 2089226N-(2-chlorobenzyl)-3-methoxyphenylacetamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 12.5 g of 3-methoxyphenylacetic acid, 21.2 g of 2-chlorobenzylamine, 15.1 g of triethylamine, 19.3 ml of borontrifluoride etherate, and 500 ml of toluene was stirred under reflux for 18 hours using a Dean-Stark moisture trap and allowed to cool. The mixture was extracted with aqueous sodium hydroxide, dilute hydrochloric acid, and water. The remaining organic solution was then evaporated and the residue crystallized from hexane to yield N-(2-chlorobenzyl)-3-methoxyphenylacetamide as a yellow solid, m.p. 89°-91° C.

Workup

  1. temperatureunder reflux for 18 hours
  2. temperatureto cool
  3. extractionThe mixture was extracted with aqueous sodium hydroxide, dilute hydrochloric acid, and water
  4. customThe remaining organic solution was then evaporated
  5. customthe residue crystallized from hexane

Sources & evidence

ORD record
ord-e5ff32d385f54149832b99453966ef75
Source dataset
uspto-grants-1986_11
Patent number
US04623662

Reaction notes

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