Sodium Hydroxide → HCID 14459257, compound

HRID 1074171Notes

Reaction equation

HRID 1074171 reaction equation
CN([C:4]([CH:6]=[CH2:7])=[O:5])C.P(Cl)(Cl)(Cl)=O.[F:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[N:21]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:22](=[O:26])[N:23]([CH3:25])[CH:24]=2)=[CH:16][CH:15]=1.[OH-].[Na+]>C(#N)C.O.C1(C)C=CC=CC=1>[F:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]2[N:21]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:22](=[O:26])[N:23]([CH3:25])[C:24]=2/[CH:7]=[CH:6]/[CH:4]=[O:5])=[CH:18][CH:19]=1

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 17587N,N-DimethylacrylamideHCID 24813Phosphorus oxychlorideHCID 14459256HCID 14459256, compound

Product 1

HCID 14459257HCID 14459257, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 6342AcetonitrileSolvent3×

Procedure

1.54 ml (14 mmol) of N,N-dimethylaminoacrolein in 5.3 ml of acetonitrile are added dropwise at 0°-5° C. in the course of 10 minutes under a nitrogen atmosphere to 1.37 ml (15 mmol) of phosphorus oxychloride in 8.5 ml of acetonitrile. After 10 minutes, a solution of 1.3 g (5 mmol) of the compound from Example 4 in 10 ml of acetonitrile is added and the mixture is heated overnight to boiling. 3.7 g of sodium hydroxide in 50 ml of water/50 ml of toluene are added at 10° C., the aqueous phase is washed again with toluene, the organic phases are dried and 0.85 g is obtained after crystallization from ether.

Workup

  1. temperaturethe mixture is heated overnight
  2. washthe aqueous phase is washed again with toluene
  3. customthe organic phases are dried
  4. custom0.85 g is obtained
  5. customafter crystallization from ether

Sources & evidence

ORD record
ord-a76be02057d845c0aff5b6b750d120f8
Source dataset
uspto-grants-1990_11
Patent number
US04973598

Reaction notes

Loading…