Triethylamine → HCID 503279, compound

HRID 326344Notes

Reaction equation

HRID 326344 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:14])=[C:6]([CH:13]=1)[C:7]([O:9][CH2:10][CH2:11][CH3:12])=[O:8].C(N(CC)CC)C.[C:22]1([CH3:31])[C:23]([C:28](Cl)=[O:29])=[CH:24][CH:25]=[CH:26][CH:27]=1>C(Cl)Cl>[Cl:14][C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:28](=[O:29])[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[CH3:31])=[CH:13][C:6]=1[C:7]([O:9][CH2:10][CH2:11][CH3:12])=[O:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 702762-Methylbenzoyl chlorideHCID 16495765HCID 16495765, compound

Product 1

HCID 503279HCID 503279, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of propyl 5-amino-2-chlorobenzoate (10.7 g, 0.050 mole) and triethylamine (6 g, 0.059 mole) in methylene chloride (50 ml) was added dropwise over 1 hour to an ice-cooled solution of o-toluoyl chloride (7.8 g, 0.50 mole) in methylene chloride (50 ml). The mixture was then stirred at room temperature for 3 hours and worked up by washing sequentially with water, dilute hydrochloric acid, water, 2% aqueous sodium hydroxide and water. The residue from evaporation of the methylene chloride was recrystallized from ethanol (100 ml) to give the title compound, m.p. 103°-105° C. (7.5 g, 45% yield).

Workup

  1. washby washing sequentially with water, dilute hydrochloric acid, water, 2% aqueous sodium hydroxide and water
  2. customThe residue from evaporation of the methylene chloride
  3. customwas recrystallized from ethanol (100 ml)

Sources & evidence

ORD record
ord-a76ce2f57d224f68b03d649f722c7dfb
Source dataset
uspto-grants-1993_12
Patent number
US05268389

Reaction notes

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