Benzoyl isothiocyanate → 3-(Benzoylcarbamothioylamino)-5-methoxy-benzoic acid

HRID 712277Notes

Reaction equation

HRID 712277 reaction equation
[C:1]([N:9]=[C:10]=[S:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:12][C:13]1[CH:14]=[C:15]([CH:19]=[C:20]([O:22][CH3:23])[CH:21]=1)[C:16]([OH:18])=[O:17]>CC(C)=O>[C:1]([NH:9][C:10]([NH:12][C:13]1[CH:14]=[C:15]([CH:19]=[C:20]([O:22][CH3:23])[CH:21]=1)[C:16]([OH:18])=[O:17])=[S:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 138744093-Amino-5-methoxybenzoic acid

Product 1

HCID 866639903-(Benzoylcarbamothioylamino)-5-methoxy-benzoic acid

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Benzoyl isothiocyanate (169 μl, 1.25 mmol) was added to a solution of 3-amino-5-methoxy-benzoic acid (0.2 g, 1.19 mmol) in acetone (10 mL). The reaction was stirred at ambient temperature and a thick precipitate formed after 10 minutes. LCMS indicated complete conversion of the starting material. The solvent was removed in vacuo and the crude material triturated with iso-hexane, dried under reduced pressure and used directly in the next step.

Workup

  1. customa thick precipitate formed after 10 minutes
  2. customThe solvent was removed in vacuo
  3. customthe crude material triturated with iso-hexane
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-574c1603f968414688ff491d6571f2b4
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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