Sodium Methoxide → 3-(Carbamothioylamino)-5-methoxy-benzoic acid

HRID 712278Notes

Reaction equation

HRID 712278 reaction equation
C[O-].[Na+].C([NH:12][C:13]([NH:15][C:16]1[CH:17]=[C:18]([CH:22]=[C:23]([O:25][CH3:26])[CH:24]=1)[C:19]([OH:21])=[O:20])=[S:14])(=O)C1C=CC=CC=1>CO>[C:13]([NH:15][C:16]1[CH:17]=[C:18]([CH:22]=[C:23]([O:25][CH3:26])[CH:24]=1)[C:19]([OH:21])=[O:20])(=[S:14])[NH2:12]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 866639903-(Benzoylcarbamothioylamino)-5-methoxy-benzoic acid

Product 1

HCID 866639913-(Carbamothioylamino)-5-methoxy-benzoic acidYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium methoxide (4.76 mL, 2.38 mmol, 0.5 M solution in methanol) was added to a solution of 3-(benzoylcarbamothioylamino)-5-methoxy-benzoic acid from Step 1 in MeOH (4 mL). The reaction was stirred at ambient temperature for 2 h after which time LCMS indicated complete conversion of the starting material. The solvent was removed in vacuo, the crude partitioned between water and DCM, the organic layer separated and the aqueous layer was acidified to pH 5 with conc HCl resulting in a thick precipitate. The precipitate was extracted into EtOAc which was then washed with brine, dried (MgSO4), filtered and concentrated in vacuo. The product was obtained as an off white solid, 248 mg, 92% yield.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe crude partitioned between water and DCM
  3. customthe organic layer separated
  4. extractionThe precipitate was extracted into EtOAc which
  5. washwas then washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe product was obtained as an off white solid, 248 mg, 92% yield

Sources & evidence

ORD record
ord-729d8b0e0bd84658a15ffb5b58070edf
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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