Hydrochloric Acid → 3-Amino-5-methylsulfanyl-benzoic acid methyl ester hydrochloride

HRID 852554Notes

Reaction equation

HRID 852554 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[C:8]([S:10][CH3:11])[CH:7]=[C:6]([NH:12]C(OC(C)(C)C)=O)[CH:5]=1.[ClH:21]>O1CCOCC1>[ClH:21].[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[C:8]([S:10][CH3:11])[CH:7]=[C:6]([NH2:12])[CH:5]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 693586183-tert-Butoxycarbonylamino-5-methylsulfanyl-benzoic acid methyl ester

Product 1

HCID 693575963-Amino-5-methylsulfanyl-benzoic acid methyl ester hydrochlorideYield 52%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

3-tert-Butoxycarbonylamino-5-methylsulfanyl-benzoic acid methyl ester (D60) (0.54 g, 1.82 mmol, 1 equiv) was dissolved in dioxan (2 ml) and 4M HCl in dioxan (16 mmol, 4 ml, 8.8 equiv) was added. The solution was stirred at room temperature for 2 h allowing the hydrochloride salt of the amine to precipitate. This precipitate was filtered off, washed with Et2O and dried giving 3-amino-5-methylsulfanyl-benzoic acid methyl ester hydrochloride (D62) (0.224 g, 52%). [M+H]+=198.1, RT=2.68 min

Workup

  1. customto precipitate
  2. filtrationThis precipitate was filtered off
  3. washwashed with Et2O
  4. customdried

Sources & evidence

ORD record
ord-6b27166b5896489ba55b64d2affd5d9e
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

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