Dimethylformamide → 2-Cyanomethyl-5-methylbenzamide

HRID 1783298Notes

Reaction equation

HRID 1783298 reaction equation
[C:1]([CH2:3][C:4]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][C:5]=1[C:6](O)=[O:7])#[N:2].C[N:15](C)C=O.C(Cl)(=O)C(Cl)=O>O1CCCC1>[C:1]([CH2:3][C:4]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][C:5]=1[C:6]([NH2:15])=[O:7])#[N:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 230848102-(Cyanomethyl)-5-methylbenzoic acid

Product 1

HCID 230847022-Cyanomethyl-5-methylbenzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Cyanomethyl-5-methylbenzoic acid (16.3 g) and dimethylformamide (0.1 mL) were suspended in tetrahydrofuran (160 mL), and oxalyl dichloride (12.2 mL) was added dropwise under ice-cooling. After cease of foaming, the solvent was evaporated. The obtained residue was dissolved in tetrahydrofuran, and the solution was added dropwise to 28% aqueous ammonia solution under ice-cooling. After the completion of the reaction, the solvent was evaporated, and the precipitated crystals were collected by filtration to give 2-cyanomethyl-5-methylbenzamide (10.9 g).

Workup

  1. temperaturecooling
  2. customthe solvent was evaporated
  3. dissolutionThe obtained residue was dissolved in tetrahydrofuran
  4. additionthe solution was added dropwise to 28% aqueous ammonia solution under ice-
  5. temperaturecooling
  6. customAfter the completion of the reaction
  7. customthe solvent was evaporated
  8. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-5302a0223cf146c2a418b84a39eda23c
Source dataset
uspto-grants-2009_03
Patent number
US07501412B2

Reaction notes

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