Methylamine → 4-cyano-N-methoxy-N-methylbenzamide

HRID 1776331Notes

Reaction equation

HRID 1776331 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7](O)=[O:8])=[CH:5][CH:4]=1)#[N:2].CN([C:15]([O:19][N:20]1N=NC2C=CC=N[C:21]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN>C(Cl)Cl.O>[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([N:20]([O:19][CH3:15])[CH3:21])=[O:8])=[CH:5][CH:4]=1)#[N:2]

Participants

6

Reactant 3

HCID 6329MethylamineHCID 120874-Cyanobenzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 110196404-cyano-N-methoxy-N-methylbenzamideYield 96%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 4-cyanobenzoic acid (5.0 g, 34.0 mmol) in DCM (75 mL) were added HATU (19.40 g, 51.0 mmol), N-methoxy, N-methylamine (4.90 g, 51.0 mmol) and TEA (14.30 mL, 102.0 mmol) at RT under a nitrogen atmosphere. The reaction mixture was then stirred at RT for 3 h, diluted with water and the aqueous layer was extracted with DCM (3×100 mL). The combined organic extracts were washed with water (60 mL) and brine (30 mL), dried over anhydrous Na2SO4, filtered and evaporated under reduced pressure to afford 4-cyano-N-methoxy-N-methylbenzamide (6.2 g, 96%) as a yellow color oil.

Workup

  1. extractionthe aqueous layer was extracted with DCM (3×100 mL)
  2. washThe combined organic extracts were washed with water (60 mL) and brine (30 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-b505161bf2634273b0005605935bb9b1
Source dataset
uspto-grants-2016_02
Patent number
US09265767B2

Reaction notes

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