Water → 2-methyl-4-[(Z)-C-methylsulfanyl-N-(trimethylsilylmethyl)carbonimidoyl]benzoic acid

HRID 1844644Notes

Reaction equation

HRID 1844644 reaction equation
C([O:5][C:6](=[O:23])[C:7]1[CH:12]=[CH:11][C:10](/[C:13](/[S:20][CH3:21])=[N:14]\[CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])=[CH:9][C:8]=1[CH3:22])(C)(C)C.FC(F)(F)C(O)=O.O>ClCCl>[CH3:22][C:8]1[CH:9]=[C:10](/[C:13](/[S:20][CH3:21])=[N:14]/[CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[CH:11]=[CH:12][C:7]=1[C:6]([OH:23])=[O:5]

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acid2×HCID 87425324tert-butyl 2-methyl-4-[(E)-C-methylsulfanyl-N-(trimethylsilylmethyl)carbonimidoyl]benzoate

Product 1

HCID 874255662-methyl-4-[(Z)-C-methylsulfanyl-N-(trimethylsilylmethyl)carbonimidoyl]benzoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-methyl-4-{methylsulfanyl-[(E)-trimethylsilanylmethylimino]-methyl}-benzoic acid tert-butyl ester (see Example I9) (118 mg) in dichloromethane (15 ml) was added trifluoroacetic acid (0.22 ml). The reaction mixture was stirred at ambient temperature for 20 hours. Further trifluoroacetic acid (0.11 ml) was added and the mixture was stirred for another 3 hours at ambient temperature. Water was added and the mixture was extracted twice with dichloromethane. The combined organic phases were washed with brine, dried over sodium sulfate and concentrated to give 2-methyl-4-{methylsulfanyl-[(Z)-trimethylsilanyl methylimino]methyl}-benzoic acid which was used without further purification in the subsequent step.

Workup

  1. stirringthe mixture was stirred for another 3 hours at ambient temperature
  2. extractionthe mixture was extracted twice with dichloromethane
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d5f1d4dcd438487c8a0d8300df5077e5
Source dataset
uspto-grants-2015_02
Patent number
US08946447B2

Reaction notes

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