Hydrochloric Acid → Methyl 4-(2-aminoethylsulfanyl)benzoate hydrochloride

HRID 2111152Notes

Reaction equation

HRID 2111152 reaction equation
C(OC([NH:8][CH2:9][CH2:10][S:11][C:12]1[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:13]=1)=O)(C)(C)C.[ClH:22].O1CCOCC1.CCOCC>ClCCl>[ClH:22].[NH2:8][CH2:9][CH2:10][S:11][C:12]1[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 312751,4-DioxaneHCID 59604290Methyl 4-(2-tert-butoxycarbonylaminoethylsulfanyl)benzoate

Product 1

HCID 66687893Methyl 4-(2-aminoethylsulfanyl)benzoate hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of methyl 4-(2-tert-butoxycarbonylaminoethylsulfanyl)benzoate (1.00 g, 3.21 mmol) in dichloromethane (8 ml) was treated with a solution of HCl in dioxane (4M, 8 ml, 10 eq.) at room temperature for 3 h. Ether (100 ml) was added and the mixture was filtered, washed with ether and pumped dry to give methyl 4-(2-aminoethylsulfanyl)benzoate hydrochloride.

Workup

  1. filtrationthe mixture was filtered
  2. washwashed with ether
  3. custompumped dry

Sources & evidence

ORD record
ord-c15010844e964919b9957de72488ed4a
Source dataset
uspto-grants-2009_04
Patent number
US07517988B2

Reaction notes

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