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Hydrochloric Acid → N-(2-ethoxycarbonyloxy-4-methoxybenzoyl)cysteamine

HRID 465916
Notes
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Reaction equation

HRID 465916 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:12])[C:6](=[CH:10][CH:11]=1)[C:7]([OH:9])=O.[C:13](Cl)(=[O:17])[O:14][CH2:15][CH3:16].[NH2:19][CH2:20][CH2:21][SH:22].Cl>C(Cl)Cl.C(N(CC)CC)C>[CH2:15]([O:14][C:13]([O:12][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[CH:11]=[CH:10][C:6]=1[C:7]([NH:19][CH2:20][CH2:21][SH:22])=[O:9])=[O:17])[CH3:16]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6058CysteamineHCID 10928Ethyl chloroformateHCID 752314-Methoxysalicylic Acid

Product 1

HCID 14719509N-(2-ethoxycarbonyloxy-4-methoxybenzoyl)cysteamineYield 89%

Reagents, catalysts & solvents 2

HCID 6344
Dichloromethane
Solvent
2×
HCID 8471TriethylamineSolvent

Conditions

Temperature
-15 °C

Procedure

Under argon atmosphere, 2.84 g of 4-methoxysalicylic acid was dispersed in 45 ml of methylene chloride, and the dispersion was cooled to -15° C. To the dispersion was added 3.76 g of triethylamine and 3.77 g of ethyl chlorocarbonate, and the mixture was agitated for 1.5 hour. To the mixture was added a solution of 1.56 g of cysteamine in 5 ml of methylene chloride, and the mixture was agitated at -15° C. for 2 hours. The reaction mixture was poured into 1N aqueous hydrochloric acid, and extracted with methylene chloride. The organic layer was washed with saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate. The solvent was distilled off in evacuated atomosphere, and the residue was subjected to column chromatography using silica gel. There was obtained 4.50 g of N-(2-ethoxycarbonyloxy-4-methoxybenzoyl)cysteamine.

Workup

  1. stirringthe mixture was agitated at -15° C. for 2 hours
  2. extractionextracted with methylene chloride
  3. washThe organic layer was washed with saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off in evacuated atomosphere

Sources & evidence

ORD record
ord-3ae318039fa6472396b71c8f4c0654bb
Source dataset
uspto-grants-1992_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05155106

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes