1,8-Diazabicyclo(5.4.0)undec-7-ene → 6-Chloro-1H-benzo[d][1,3]oxazin-2(4H)-one

HRID 1710669Notes

Reaction equation

HRID 1710669 reaction equation
C([O:3][C:4](=[O:15])[NH:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][C:7]=1[CH2:13]O)C.C1CCN2C(=NCCC2)CC1>C1(C)C=CC=CC=1.CCOC(C)=O>[Cl:12][C:9]1[CH:10]=[CH:11][C:6]2[NH:5][C:4](=[O:3])[O:15][CH2:13][C:7]=2[CH:8]=1

Participants

5

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 58834345(4-Chloro-2-hydroxymethyl-phenyl)-carbamic acid ethyl ester

Product 1

HCID 111947166-Chloro-1H-benzo[d][1,3]oxazin-2(4H)-one

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (4-chloro-2-hydroxymethyl-phenyl)-carbamic acid ethyl ester (71) obtained from the previous step in 5 mL of toluene was added 3 mL of DBU (2 equiv) and the resultant solution was heated at 110° C. overnight. After cooling to rt, the mixture was diluted with EtOAc and washed with water. The organic layer was dried over sodium sulfate, filtered and dried in vacuo to give 6-chloro-1,4-dihydro-benzo[d][1,3]oxazin-2-one (72).

Workup

  1. washwashed with water
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. customdried in vacuo

Sources & evidence

ORD record
ord-9af77a1f28a049758b712de23ec63b7c
Source dataset
uspto-grants-2010_09
Patent number
US07790726B2

Reaction notes

Loading…