Water → HCID 58778976, compound

HRID 1372609Notes

Reaction equation

HRID 1372609 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[S:33])[NH:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:13][C:12]=1SCC1C=CC(OC)=CC=1.O>C(O)C>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[S:33][C:12]2[CH:13]=[C:14]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:15]=[CH:16][C:11]=2[N:10]=1

Participants

4

Reactant 2

HCID 962WaterHCID 58778491HCID 58778491, compound

Product 1

HCID 58778976HCID 58778976, compoundYield 83.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In ethanol (50 ml), ethyl 4-(N′-(2-methylphenyl)thioureido)-3-(4-methoxybenzylthio)phenylacetate (1.63 g, 3.40 mmol) and mercuric oxide (yellow) (1.10 g, 16.4 mmol) were stirred for one hour at 70° C. Water (50 ml) was added and the mixture was extracted with ethyl acetate. The extract was washed with water and a saturated aqueous solution of sodium bicarbonate, dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column, whereby from hexane-ethyl acetate (3:1) eluate fractions, ethyl 2-(2-methylphenylamino)-6-benzothiazolylacetate (922 mg, 83%) was obtained as a pale yellow oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materiala saturated aqueous solution of sodium bicarbonate, dried over anhydrous sodium sulfate
  4. distillationdistilled under reduced pressure
  5. customto remove the solvent
  6. customThe residue was purified by chromatography on a silica gel column, whereby from hexane-ethyl acetate (3:1) eluate fractions

Sources & evidence

ORD record
ord-c8842f8b8dd146f2b75e17fcc53c9243
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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