Water → HCID 22258909, compound

HRID 1611214Notes

Reaction equation

HRID 1611214 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[NH:20][C:19](=[O:21])[C:18]([C:22]#[N:23])=[C:17]([S:24]([CH3:26])=[O:25])[CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:28][C:29]([NH2:31])=[O:30].C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[N:20]=[C:19]([O:21][CH2:28][C:29]([NH2:31])=[O:30])[C:18]([C:22]#[N:23])=[C:17]([S:24]([CH3:26])=[O:25])[CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 696322-BromoacetamideHCID 22258920HCID 22258920, compound

Product 1

HCID 22258909HCID 22258909, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 6-[2-(benzyloxy)phenyl]-4-(methylsulfinyl)-2-oxo-1,2-dihydro-3-pyridinecarbonitrile (2.97 g, 8.16 mmol), bromoacetamide (1.27 g, 9.21 mmol), and K2CO3 (1.43 g, 10.4 mmol) in DMF (30 mL) was stirred at 60° C. for 1.5 hrs. The reaction mixture was poured into water, and the resulting precipitates were collected by filtration. The solid obtained was washed with acetone to give 2-{[6-[2-(benzyloxy)phenyl]-3-cyano-4-(methylsulfinyl)-2-pyridinyl]oxy}acetamide as a solid (2.09 g, yield; 61%).

Workup

  1. customthe resulting precipitates
  2. filtrationwere collected by filtration
  3. customThe solid obtained
  4. washwas washed with acetone

Sources & evidence

ORD record
ord-457544aeb64449ff91882fba81ee89c2
Source dataset
uspto-grants-2006_01
Patent number
US06984649B1

Reaction notes

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