Dimethylformamide → 4-(tetrahydropyran-4-ylmethyl)-6-amino-3,4-dihydro-2H-1,4-benzoxazin-3-one

HRID 249189Notes

Reaction equation

HRID 249189 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][C:8](=[O:11])[NH:7][C:6]=2[CH:12]=1.CN(C)C=O.[H-].[Na+].Br[CH2:21][CH:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1>O>[O:25]1[CH2:26][CH2:27][CH:22]([CH2:21][N:7]2[C:6]3[CH:12]=[C:2]([NH2:1])[CH:3]=[CH:4][C:5]=3[O:10][CH2:9][C:8]2=[O:11])[CH2:23][CH2:24]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 27636816-amino-3,4-dihydro-2H-1,4-benzoxazin-3-oneHCID 27732864-(Bromomethyl)oxane

Product 1

HCID 144414614-(tetrahydropyran-4-ylmethyl)-6-amino-3,4-dihydro-2H-1,4-benzoxazin-3-oneYield 64%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4.9 g (0.03 mol) of 6-amino-3,4-dihydro-2H-1,4-benzoxazin-3-one is introduced into 50 ml of dimethylformamide. At 5° C., 0.79 g (0.033 mol) of sodium hydride is added, and the mixture is stirred for 30 minutes at this temperature. Subsequently, 5.9 g (0.033 mol) of 4-bromomethyltetrahydropyran is added, the mixture is stirred for 3 hours at 60° C., 200 ml of water is added, extraction is carried out twice with methylene chloride, followed by drying and evaporation of the solvent under reduced pressure. There is obtained 5 g (64%) of 4-(tetrahydropyran-4-ylmethyl)-6-amino-3,4-dihydro-2H-1,4-benzoxazin-3-one as an oil.

Workup

  1. stirringthe mixture is stirred for 3 hours at 60° C.
  2. extractionextraction
  3. customby drying
  4. customevaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-5fa8ee3feb184766b9f94cb19b21f45b
Source dataset
uspto-grants-1993_05
Patent number
US05213605

Reaction notes

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