Water → 6-(Benzyloxy)-8-(bromoacetyl)-2H-1,4-benzoxazin-3(4H)-one

HRID 1967187Notes

Reaction equation

HRID 1967187 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].[Br-:23].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.O>O1CCOCC1.CO>[Br:23][CH2:2][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]

Participants

6

Reactant 3

HCID 962WaterHCID 211001368-Acetyl-6-(benzyloxy)-2H-1,4-benzoxazin-3(4H)-oneHCID 23500184Tetra-n-butylammonium tribromide

Product 1

HCID 442495926-(Benzyloxy)-8-(bromoacetyl)-2H-1,4-benzoxazin-3(4H)-one

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
20 °C

Procedure

12.00 kg (40.36 mol) 8-acetyl-6-(phenylmethoxy)-2H-1,4-benzoxazin-3(4H)-one 3a are dissolved in 108 l 1,4-dioxane. Then a solution of 24.33 kg (50.45 mol) tetrabutylammonium tribromide in 48 l of 1,4-dioxane and 12 l methanol is metered into the suspension at 20° C. The reactor contents are stirred for 2 hours at 20° C. Then 72 l water are added at 20° C. within 15 minutes. After cooling to 3° C. the mixture is stirred for 1 hour, centrifuged and washed with a mixture of 9 l of 1,4-dioxane and 4.5 l water. Then it is washed with 60 l water and dried in vacuo at 50° C.

Workup

  1. customis metered into the suspension at 20° C
  2. temperatureAfter cooling to 3° C. the mixture
  3. stirringis stirred for 1 hour
  4. washcentrifuged and washed with a mixture of 9 l of 1,4-dioxane and 4.5 l water
  5. washThen it is washed with 60 l water
  6. customdried in vacuo at 50° C.

Sources & evidence

ORD record
ord-c5b077c28b6e46feb82723cd570e9d8c
Source dataset
uspto-grants-2013_04
Patent number
US08420809B2

Reaction notes

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