Formamide → N-((2,5-Difluorophenyl)(tosyl)methyl)formamide

HRID 1929965Notes

Reaction equation

HRID 1929965 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([OH:10])=[O:9])=[CH:4][CH:3]=1.[F:11][C:12]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:13]=1[CH:14]=O.[CH:21]([NH2:23])=[O:22]>CO.[C@]12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O>[F:11][C:12]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:13]=1[CH:14]([S:8]([C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=1)(=[O:10])=[O:9])[NH:23][CH:21]=[O:22]

Participants

6

Reactant 3

HCID 713FormamideHCID 10818p-Toluenesulfinic acidHCID 1376632,5-Difluorobenzaldehyde

Product 1

HCID 22170178N-((2,5-Difluorophenyl)(tosyl)methyl)formamideYield 56.9%

Reagents, catalysts & solvents 2

HCID 218580(1S)-(+)-Camphor-10-sulphonic acidCatalystHCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

To a round bottom flask was added 4-methylbenzenesulfinic acid (5.00 g, 32.0 mmol, Preparation #3, Step A), (1S)-(+)-10-camphorsulfonic acid (0.074 g, 0.32 mmol), 2,5-difluorobenzaldehyde (3.83 mL, 35.2 mmol) and formamide (6.38 mL, 160 mmol). The reaction mixture was stirred at about 65° C. for about 16 h. The reaction mixture had solidified overnight. The solid was broken up and suspended in MeOH. The chunks of solid were ground to a powder with a spatula and the solid was filtered and washed with MeOH. The filter cake was dried under vacuum at about 60° C. to give the title compound (5.92 g, 56.8%) as a white powder. LC/MS (Table 1, Method a) Rt=2.37 min; MS m/z: 343.1 (M+NH3)+.

Workup

  1. waitThe reaction mixture had solidified overnight
  2. filtrationthe solid was filtered
  3. washwashed with MeOH
  4. customThe filter cake was dried under vacuum at about 60° C.

Sources & evidence

ORD record
ord-96cb5cb914944b18b46f1c5841019810
Source dataset
uspto-grants-2012_05
Patent number
US08188083B2

Reaction notes

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