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

HRID 727749Notes

Reaction equation

HRID 727749 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.[H-].[Na+].BrC[CH:17]1[CH2:22][CH2:21][CH2:20][O:19][CH2:18]1.O.[CH3:24]N(C)C=O>>[O:19]1[CH2:18][CH2:17][CH:22]([CH2:24][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])[CH2:21][CH2:20]1

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 27636816-amino-3,4-dihydro-2H-1,4-benzoxazin-3-oneHCID 226172573-(Bromomethyl)oxane

Product 1

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

Procedure

4.9 g (0.03 mole) of 6-amino-3,4-dihydro-2H-1,4-benzoxazin-3-one in 50 ml of dimethylformamide are initially taken, 0.79 g (0.033 mole) of sodium hydride is added at 5° C. and the mixture is stirred for 30 minutes at this temperature. Thereafter, 5.9 g (0.033 mole) of 3-bromomethyltetrahydropyran are added, stirring is continued for 3 hours at 60° C., 200 ml of water are added the mixture is extracted twice with 200 ml of methylene chloride, the extracts are dried and the solvent is evaporated under reduced pressure. 5 g (64%) of 4-(tetrahydropyran-4-ylmethyl)-6-amino-3,4-dihydro-2H-1,4-benzoxazin-3-one (oil) are obtained.

Workup

  1. stirringstirring
  2. waitis continued for 3 hours at 60° C.
  3. extractionis extracted twice with 200 ml of methylene chloride
  4. customthe extracts are dried
  5. customthe solvent is evaporated under reduced pressure

Sources & evidence

ORD record
ord-c62f77911d05488fae93304d6e3bd5f5
Source dataset
uspto-grants-1991_09
Patent number
US05045105

Reaction notes

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