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

HRID 2402766Notes

Reaction equation

HRID 2402766 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-34357928367c46b6b1bbcaa14f0b5c38
Source dataset
uspto-grants-2014_08
Patent number
US08796324B2

Reaction notes

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