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Hydrochloric Acid → N-(2,6-diisopropylphenyl)-2-(ethoxycarbonylmethylthio)acetamide

HRID 36764
Notes
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Reaction equation

HRID 36764 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]([CH3:12])[CH3:11])[C:5]=1[NH:13][C:14](=[O:17])[CH2:15]Cl)([CH3:3])[CH3:2].[SH:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21].C(=O)([O-])[O-].[K+].[K+].Cl>O.CS(C)=O>[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]([CH3:12])[CH3:11])[C:5]=1[NH:13][C:14](=[O:17])[CH2:15][S:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])([CH3:3])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 12185Ethyl ThioglycolateHCID 23637742-Chloro-N-(2,6-diisopropylphenyl)acetamide

Product 1

HCID 2468543N-(2,6-diisopropylphenyl)-2-(ethoxycarbonylmethylthio)acetamideYield 90.4%

Reagents, catalysts & solvents 2

HCID 679
Dimethyl Sulfoxide
Solvent
HCID 962WaterSolvent

Procedure

A mixture of 18.8 g of N-(2,6-diisopropylphenyl)-2-chloroacetamide, 8.9 g of ethyl 2-mercaptoacetate, 20.4 g of potassium carbonate, and 100 ml of dimethyl sulfoxide was stirred at room temperature for 1 hour, and a mixture of 25 ml of concentrated hydrochloric acid and 100 ml of water was added thereto. The reaction mixture was extracted with 300 ml of ethyl acetate, and the extract was washed successively with a 1N hydrochloric acid aqueous solution, a sodium hydrogencarbonate aqueous solution, and a saturated sodium chloride aqueous solution, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure to yield 22.6 g of N-(2,6-diisopropylphenyl)-2-(ethoxycarbonylmethylthio)acetamide as white needle crystals (m.p.=124.0°-125.0° C.).

Workup

  1. additionwas added
  2. extractionThe reaction mixture was extracted with 300 ml of ethyl acetate
  3. washthe extract was washed successively with a 1N hydrochloric acid aqueous solution
  4. dry with materiala sodium hydrogencarbonate aqueous solution, and a saturated sodium chloride aqueous solution, and dried over magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-11382ea09c7744b4973a8e55772bb9d8
Source dataset
uspto-grants-1995_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05416212

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes