Formamide → HCID 11438410, compound

HRID 2202099Notes

Reaction equation

HRID 2202099 reaction equation
[CH:1]([C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1)=O.[CH:11]([NH2:13])=[O:12].[CH3:14][C:15]1[CH:20]=[CH:19][C:18]([S:21]([OH:23])=[O:22])=[CH:17][CH:16]=1.Cl[Si](C)(C)C>C1(C)C=CC=CC=1.CC#N.O>[C:7]([C:6]1[CH:9]=[CH:10][C:3]([CH:1]([S:21]([C:18]2[CH:19]=[CH:20][C:15]([CH3:14])=[CH:16][CH:17]=2)(=[O:23])=[O:22])[NH:13][CH:11]=[O:12])=[CH:4][CH:5]=1)#[N:8]

Participants

8

Reactant 4

HCID 713FormamideHCID 6397ChlorotrimethylsilaneHCID 10818p-Toluenesulfinic acidHCID 660424-Cyanobenzaldehyde

Product 1

HCID 11438410HCID 11438410, compoundYield 48.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of 4-formylbenzonitrile (5.2 g, 39.65 mmol, 1.00 equiv), formamide (4.5 g, 99.91 mmol, 2.52 equiv), 4-methylbenzene-1-sulfinic acid (8.7 g, 55.70 mmol, 1.40 equiv) and chlorotrimethylsilane (6.5 g, 59.83 mmol, 1.51 equiv) in toluene (5 mL) and CH3CN (5 mL) was stirred at 50° C. for 26 h. The resulting solution was diluted with 100 mL of water and then extracted with 3×50 mL of ethyl acetate. The organic layers were combined then washed with 3×50 mL of water and 2×50 mL of brine. It was then dried over anhydrous sodium sulfate and concentrated under vacuum to give 6 g of crude N-((4-cyanophenyl)(tosyl)methyl)formamide as a light brown solid.

Workup

  1. extractionextracted with 3×50 mL of ethyl acetate
  2. washThe organic layers were combined then washed with 3×50 mL of water and 2×50 mL of brine
  3. dry with materialIt was then dried over anhydrous sodium sulfate
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-d92dab2fa4a34142b320e594f8030eaf
Source dataset
uspto-grants-2016_06
Patent number
US09365527B2

Reaction notes

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