HCID 18353297, compound → Methyl 2-(m-methylbenzylthio)-5-trifluoromethylbenzoate

HRID 978087Notes

Reaction equation

HRID 978087 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][CH:22]=1)[CH2:5][S:6][C:7]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][C:8]=1[C:9]([OH:11])=[O:10].NO[C:25]1CCCCCC=1>C(OCC)C>[CH3:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][CH:22]=1)[CH2:5][S:6][C:7]1[CH:15]=[CH:14][C:13]([C:16]([F:17])([F:18])[F:19])=[CH:12][C:8]=1[C:9]([O:11][CH3:25])=[O:10]

Participants

4

Reactant 2

HCID 18353297HCID 18353297, compoundHCID 202050722-(m-Methylbenzylthio)-5-trifluoromethylbenzoic acid

Product 1

HCID 13787728Methyl 2-(m-methylbenzylthio)-5-trifluoromethylbenzoate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 2-(m-methylbenzylthio)-5-trifluoromethylbenzoic acid (1.65 g, 5.06 mmol) and 1-aza-2-methoxy-1-cycloheptene (643 mg, 5.06 mmol) was heated at 80°-85° C. for 18 hours, cooled, diluted with diethyl ether, washed with 1N aqueous sodium hydroxide solution, water, dried (sodium sulfate), and evaporated. The product was crystallized from methanol; yield 885 mg (51%). The 60 MHz NMR spectrum in chloroform-d was in accord with the desired structure.

Workup

  1. temperaturewas heated at 80°-85° C. for 18 hours
  2. temperaturecooled
  3. washwashed with 1N aqueous sodium hydroxide solution, water
  4. dry with materialdried (sodium sulfate)
  5. customevaporated
  6. customThe product was crystallized from methanol

Sources & evidence

ORD record
ord-a03ea212e42c44d9a79ad93b0a770a3e
Source dataset
uspto-grants-1987_05
Patent number
US04663344

Reaction notes

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