Acetic Acid → 8-(2-Chloroacetyl)-6-(phenylmethoxy)-2H-1,4-benzoxazin-3(4H)-one

HRID 1352209Notes

Reaction equation

HRID 1352209 reaction equation
[C:1]([C:4]1[C:13]2[O:12][CH2:11][C:10](=[O:14])[NH:9][C:8]=2[CH:7]=[C:6]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:5]=1)(=[O:3])[CH3:2].C(O)(=O)C.O.S([O-])(O)=O.[Na+].[Cl:33]C(Cl)C>>[CH2:16]([O:15][C:6]1[CH:5]=[C:4]([C:1](=[O:3])[CH2:2][Cl:33])[C:13]2[O:12][CH2:11][C:10](=[O:14])[NH:9][C:8]=2[CH:7]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 962WaterHCID 63651,1-DichloroethaneHCID 211001368-Acetyl-6-(benzyloxy)-2H-1,4-benzoxazin-3(4H)-oneHCID 23665763Sodium Bisulfite

Product 1

HCID 211001328-(2-Chloroacetyl)-6-(phenylmethoxy)-2H-1,4-benzoxazin-3(4H)-one

Procedure

13.8 g (46.0 mmol) 8-acetyl-6-benzyloxy-4H-benzo[1,4]oxazin-3-one and 35.3 g (101.5 mmol) benzyltrimethylammonium-dichloriodate are stirred in 250 mL dichloroethane, 84 mL glacial acetic acid and 14 mL water for 5 hours at 65° C. After cooling to ambient temperature the mixture is combined with 5% sodium hydrogen sulphite solution and stirred for 30 minutes. The precipitated solid is suction filtered, washed with water and diethyl ether and dried. Yield: 13.2 g (86%); mass spectroscopy [M+H]+=330/32.

Workup

  1. filtrationfiltered
  2. washwashed with water and diethyl ether
  3. customdried

Sources & evidence

ORD record
ord-af708ae5e2254a179faa1f594ff9131a
Source dataset
uspto-grants-2007_05
Patent number
US07220742B2

Reaction notes

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