Chlorosuccinimide → 4-Acetylamino-5-chloro-2-hexyloxybenzoic acid methyl ester

HRID 1608231Notes

Reaction equation

HRID 1608231 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:13])[CH3:12])=[CH:6][C:5]=1[O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].[Cl:22]N1C(=O)CCC1=O>CN(C)C=O>[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[C:8]([Cl:22])[C:7]([NH:10][C:11](=[O:13])[CH3:12])=[CH:6][C:5]=1[O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 543827224-Acetylamino-2-hexyloxybenzoic acid methyl ester

Product 1

HCID 543884334-Acetylamino-5-chloro-2-hexyloxybenzoic acid methyl esterYield 72.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of 4-acetylamino-2-hexyloxybenzoic acid methyl ester (2.6 g) in dimethylformamide (20 ml) is added N-chlorosuccinimide (1.4 g), and the resulting mixture is stirred at 70° C. for 1 hour. The reaction mixture is poured into ice-water and extracted with diethyl ether. The organic layer is washed successively with water and saturated sodium chloride solution, dried over magnesium sulfate, and evaporated to give 4-acetylamino-5-chloro-2-hexyloxybenzoic acid methyl ester (2.1 g) as an oil.

Workup

  1. extractionextracted with diethyl ether
  2. washThe organic layer is washed successively with water and saturated sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-73c4776ce0f749f2b6fd757c8ee7631e
Source dataset
uspto-grants-1989_09
Patent number
US04870074

Reaction notes

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