Ethanolamine → HCID 21511936, compound

HRID 1576319Notes

Reaction equation

HRID 1576319 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([C:9]1[CH:14]=[C:13]([Br:15])[CH:12]=[CH:11][C:10]=1[NH:16][C:17](=[O:22])C(Cl)(Cl)Cl)=[O:8].[CH2:23]([CH2:25][NH2:26])O.O>CS(C)=O>[Br:15][C:13]1[CH:12]=[CH:11][C:10]2[NH:16][C:17](=[O:22])[N:26]3[CH2:25][CH2:23][O:8][C:7]3([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)[C:9]=2[CH:14]=1

Participants

5

Reactant 3

HCID 700EthanolamineHCID 962WaterHCID 12427470HCID 12427470, compound

Product 1

HCID 21511936HCID 21511936, compoundYield 57.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 1.27 g of 2-trichloroacetamido-5-bromophenyl 2-pyridyl ketone in 20 ml of dimethylsulfoxide was added 1.83 g of monoethanolamine, and the resultant mixture was heated in an oil bath at 100°C (bath temperature) for 3 hours. After cooling, the reaction mixture was poured into 100 ml of water and the resulting mixture was extracted with dichloromethane. The extract was washed with water and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure. The residue was chromatographed on silica gel using chloroform as an eluent to give 0.6 g of 9-bromo-2,3,6,10b-tetrahydro-10b-(2-pyridyl)-5H-oxazolo[3,2-C]quinazolin-5-one, having a melting point of 241° - 242°C.

Workup

  1. temperatureAfter cooling
  2. extractionthe resulting mixture was extracted with dichloromethane
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-93c5bd464c1c41a5922234d37b189ecf
Source dataset
uspto-grants-1976_09
Patent number
US03980645

Reaction notes

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