Formic Acid → tert-Butyl {(phenylsulphonyl)[3-(trifluoromethyl)phenyl]methyl}carbamate

HRID 220630

Reaction equation

HRID 220630 reaction equation
[C:1](=[O:8])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])[NH2:2].[C:9]1([S:15]([O-:17])=[O:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[Na+].[F:19][C:20]([F:30])([F:29])[C:21]1[CH:22]=[C:23]([CH:27]=O)[CH:24]=[CH:25][CH:26]=1.C(O)=O>CO.O>[C:9]1([S:15]([CH:27]([NH:2][C:1](=[O:8])[O:3][C:4]([CH3:7])([CH3:6])[CH3:5])[C:23]2[CH:24]=[CH:25][CH:26]=[C:21]([C:20]([F:19])([F:29])[F:30])[CH:22]=2)(=[O:17])=[O:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 284Formic AcidHCID 679903-(Trifluoromethyl)benzaldehydeHCID 77922tert-Butyl carbamateHCID 2723840Benzenesulfinic acid, sodium salt

Product 1

HCID 59536907tert-Butyl {(phenylsulphonyl)[3-(trifluoromethyl)phenyl]methyl}carbamate

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

A quantity of 4.49 g (38.29 mmol) of tert-butyl carbamate and 12.57 g (76.57 mmol) of sodium benzenesulphinate were introduced in 110 ml of methanol/water 1:2 and admixed in succession with 10 g (57.43 mmol) of 3-(trifluoromethyl)benzenecarbaldehyde and 2.87 ml (76.09 mmol) of formic acid. The mixture was stirred at RT for 30 h. The precipitated product was isolated by filtration, washed in succession with water and diethyl ether and sucked dry. Further drying in an HV gave 11.2 g (47% of theory) of the title compound.

Workup

  1. customThe precipitated product was isolated by filtration
  2. washwashed in succession with water and diethyl ether
  3. customsucked dry
  4. customFurther drying in an HV

Sources & evidence

ORD record
ord-dd01c49f80e34d9485cb26a159e4f399
Source dataset
uspto-grants-2012_06
Patent number
US08202895B2

Linked notes

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