Triethylamine → HCID 507313, compound

HRID 1938855Notes

Reaction equation

HRID 1938855 reaction equation
[CH3:1][C:2]1[CH:6]=[CH:5][O:4][C:3]=1[C:7](Cl)=[O:8].[NH2:10][C:11]1[CH:12]=[CH:13][C:14]([Cl:23])=[C:15]([CH:22]=1)[C:16]([O:18][CH:19]([CH3:21])[CH3:20])=[O:17].C(N(CC)CC)C>C1(C)C=CC=CC=1>[Cl:23][C:14]1[CH:13]=[CH:12][C:11]([NH:10][C:7]([C:3]2[O:4][CH:5]=[CH:6][C:2]=2[CH3:1])=[O:8])=[CH:22][C:15]=1[C:16]([O:18][CH:19]([CH3:21])[CH3:20])=[O:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 369590Isopropyl 5-amino-2-chlorobenzoateHCID 27966743-Methylfuran-2-carbonyl chloride

Product 1

HCID 507313HCID 507313, compoundYield 47.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Procedure

A solution of 3-methyl-2-furancarbonyl chloride (9.5 g, 0.066 mole) in toluene (20 ml) was added to 1-methylethyl 5-amino-2-chlorobenzoate (14 g, 0.066 mole) and triethylamine (10 g) in toluene (20 ml). After about three hours at ambient temperature, the mixture was washed with dilute hydrochloric acid, water, aqueous 5% sodium bicarbonate and finally water. With cooling, the product (m.p. 99°-100° C., 10 g, 47% yield) was crystallized from toluene.

Workup

  1. washthe mixture was washed with dilute hydrochloric acid, water, aqueous 5% sodium bicarbonate and finally water
  2. temperatureWith cooling

Sources & evidence

ORD record
ord-bc6f91b0017340818c148a6279e12565
Source dataset
uspto-grants-1997_12
Patent number
US05693827

Reaction notes

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