N-methoxy-N-methylcarbamoyl chloride → HCID 14500904, compound

HRID 1032615Notes

Reaction equation

HRID 1032615 reaction equation
[CH3:1][C:2]1([CH3:20])[CH2:6][C:5]2[CH:7]=[CH:8][CH:9]=[C:10]([CH2:11][O:12][C:13]3[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][N:14]=3)[C:4]=2[O:3]1.[CH3:21][O:22][N:23]([CH3:27])[C:24](Cl)=[O:25]>N1C=CC=CC=1>[CH3:1][C:2]1([CH3:20])[CH2:6][C:5]2[CH:7]=[CH:8][CH:9]=[C:10]([CH2:11][O:12][C:13]3[CH:18]=[CH:17][C:16]([NH:19][C:24]([N:23]([O:22][CH3:21])[CH3:27])=[O:25])=[CH:15][N:14]=3)[C:4]=2[O:3]1

Participants

4

Reactant 2

HCID 2734926N-methoxy-N-methylcarbamoyl chlorideHCID 14500903HCID 14500903, compound

Product 1

HCID 14500904HCID 14500904, compoundYield 83.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2.0 g of 2-(2,3-dihydro-2,2-dimethyl-7-benzofuranylmethyloxy)-5-aminopyridine was dissolved into 5 ml of pyridine, and 1.1 g of N-methoxy-N-methylcarbamoyl chloride was slowly added dropwise thereto under cooling with ice. After 2-hours' continuous stirring, pyridine was distilled off under a reduced pressure, and the residual oily matter was dissolved into 30 ml of toluene. After the mixture was subsequently washed with water, diluted hydrochloric acid and saturated sodium chloride aqueous solution, toluene was distilled off. The residue was subjected to silica gel column chromatography using ethyl acetate/n-hexane (1/1) as a developer to obtain 2.2 g of 1-[2-(2,3-dihydro-2,2-dimethyl-7-benzofuranylmethyloxy)-5-pyridyl]-3-methoxy-3-methylurea.

Workup

  1. additionwas slowly added dropwise
  2. temperatureunder cooling with ice
  3. distillationAfter 2-hours' continuous stirring, pyridine was distilled off under a reduced pressure
  4. dissolutionthe residual oily matter was dissolved into 30 ml of toluene
  5. washAfter the mixture was subsequently washed with water, diluted hydrochloric acid and saturated sodium chloride aqueous solution, toluene
  6. distillationwas distilled off

Sources & evidence

ORD record
ord-a591f3d5c28846d6a6c296acf77f940c
Source dataset
uspto-grants-1990_09
Patent number
US04959092

Reaction notes

Loading…