3-Amino-1-propanol → HCID 12750805, compound

HRID 1576323Notes

Reaction equation

HRID 1576323 reaction equation
ClC(Cl)(Cl)[C:3]([NH:5][C:6]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:7]=1[C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:9])=[O:4].[NH2:23][CH2:24][CH2:25][CH2:26]O.[OH-].[K+]>C(O)C>[Cl:20][C:17]1[CH:18]=[CH:19][C:6]2[NH:5][C:3](=[O:4])[N:23]3[CH2:24][CH2:25][CH2:26][O:9][C:8]3([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:7]=2[CH:16]=1

Participants

5

Reactant 3

HCID 90863-Amino-1-propanolHCID 14797Potassium HydroxideHCID 306974STK173631

Product 1

HCID 12750805HCID 12750805, compoundYield 104.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 11.3 g of 2-trichloroacetamido-5-chlorobenzophenone in 100 ml. of ethanol was added 4.51 g of 3-amino-1-propanol. The mixture was heated under reflux for 3 hours. Then, 1.7 g of potassium hydroxide was added thereto and the resulting mixture was further refluxed for 3 hours. After cooling, the precipitate was filtered off and washed with ethanol. The filtrate was concentrated under reduced pressure and to the residue was added 200 ml. of water. The resulting solid was collected by filtration, washed with water and dried to give 9.87 g of 10-chloro-3,4,7,11b-tetrahydro-11b-phenyl-2H,6H-[1,3]oxazino[3,2-C]quinazolin-6-one. Recrystallization from ethanol gave pale yellow prisms, having a melting point of 202°-203.5°C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. temperaturethe resulting mixture was further refluxed for 3 hours
  4. temperatureAfter cooling
  5. filtrationthe precipitate was filtered off
  6. washwashed with ethanol
  7. concentrationThe filtrate was concentrated under reduced pressure and to the residue
  8. additionwas added 200 ml
  9. filtrationThe resulting solid was collected by filtration
  10. washwashed with water
  11. customdried

Sources & evidence

ORD record
ord-54bdbcf29d524c79a1ed1331455a76bd
Source dataset
uspto-grants-1976_09
Patent number
US03980645

Reaction notes

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