Water → HCID 86628979, compound

HRID 499284Notes

Reaction equation

HRID 499284 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([OH:12])[C:5](=[CH:10][CH:11]=1)[C:6]([O:8][CH3:9])=[O:7].C[N:14](C)[C:15](Cl)=[S:16].[N:19]12CCN(CC1)C[CH2:20]2.O.[CH3:28][N:29](C=O)C>>[CH3:20][NH:19][N:14]([NH:29][CH3:28])[C:15]([O:12][C:4]1[CH:3]=[C:2]([CH3:1])[CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7])=[S:16]

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 9237DabcoHCID 27871Dimethylthiocarbamoyl chlorideHCID 78400Benzoic acid, 2-hydroxy-4-methyl-, methyl ester

Product 1

HCID 86628979HCID 86628979, compoundYield 55%

Procedure

Methyl 4-methylsalicylate (10.7 g, 64 mmol) was dissolved in DMF (100 ml). N,N-Dimethylthiocarbamoyl chloride (8.0 g, 65 mmol) and 1,4-diazabicyclo[2,2,2]octane (7.2 g, 65 mmol) were added thereto with the mixture stirring. The reaction mixture was stirred at room temperature for 20 hrs, poured into water and extracted with ethyl acetate. The extract was washed with water and dried, and the solvent was evaporated under reduced pressure. The residue was subjected to a silica gel column chromatography, eluted with hexane-ethyl acetate (3:1, v/v), recrystallized from ethyl acetate-hexane to give methyl 2-(N,N-dimethylaminothiocarbamoyl)oxy-4-methylbenzoate (9.1 g, 55%) as crystals (mp. 99.9-100.2° C.).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 20 hrs
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. customdried
  5. customthe solvent was evaporated under reduced pressure
  6. washeluted with hexane-ethyl acetate (3:1
  7. customv/v), recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-5df90024e5734496b24c9aa29db5f5dd
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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