Ethanethiol → Ethyl 2-[[4-hydroxybenzenesulfonyl](isobutyl)amino]acetate

HRID 2209706Notes

Reaction equation

HRID 2209706 reaction equation
C(S)C.[Cl-].[Cl-].[Cl-].[Al+3].C[O:9][C:10]1[CH:15]=[CH:14][C:13]([S:16]([N:19]([CH2:26][CH:27]([CH3:29])[CH3:28])[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])(=[O:18])=[O:17])=[CH:12][CH:11]=1>C(Cl)Cl>[OH:9][C:10]1[CH:15]=[CH:14][C:13]([S:16]([N:19]([CH2:26][CH:27]([CH3:28])[CH3:29])[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])(=[O:18])=[O:17])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 6451240Aluminum(III) ChlorideHCID 10640094Ethyl 2-[[4-methoxybenzenesulfonyl](isobutyl)amino]acetate

Product 1

HCID 10591435Ethyl 2-[[4-hydroxybenzenesulfonyl](isobutyl)amino]acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of ethanethiol (15 mL) and methylene chloride (15 mL) is cooled to 0° C. Aluminum trichloride (9.62 g, 72.2 mmol) is added (the solution turns green), and the reaction is warmed to room temperature. Ethyl 2-[[4-methoxybenzenesulfonyl](isobutyl)amino]acetate (4.75 g, 14.44 mmol) is added in methylene chloride (5 mL), and the reaction is stirred for 3.5 hours at room temperature. The reaction is then slowly quenched with water, and the crude reaction is partitioned between water and methylene chloride. The aqueous layer is extracted well with methylene chloride, the combined organic layers are dried (Na2SO4), and the solvent is evaporated. The product is purified by silica gel chromatography (25% to 50% ethyl acetate/hexane) to give ethyl 2-[[4-hydroxybenzenesulfonyl](isobutyl)amino]acetate.

Workup

  1. customThe reaction is then slowly quenched with water
  2. customthe crude reaction
  3. customis partitioned between water and methylene chloride
  4. extractionThe aqueous layer is extracted well with methylene chloride
  5. dry with materialthe combined organic layers are dried (Na2SO4)
  6. customthe solvent is evaporated
  7. customThe product is purified by silica gel chromatography (25% to 50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-f3ebab5c6d1a46a18b317043078c8469
Source dataset
uspto-grants-1995_10
Patent number
US05455258

Reaction notes

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