Water → HCID 19377624, compound

HRID 1609467Notes

Reaction equation

HRID 1609467 reaction equation
[C:1]([C:9]1[C:14]2[NH:15][CH2:16][CH2:17][O:18][C:13]=2[CH:12]=[CH:11][CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[Br:25][CH2:26][C:27](Br)=[O:28].O>C(Cl)Cl>[Br:25][CH2:26][C:27]([N:15]1[C:14]2[C:9]([C:1](=[O:8])[C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:10][CH:11]=[CH:12][C:13]=2[O:18][CH2:17][CH2:16]1)=[O:28]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 61147Bromoacetyl bromideHCID 19377627HCID 19377627, compound

Product 1

HCID 19377624HCID 19377624, compoundYield 69.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5-benzoyl-3,4-dihydro-2H-1,4-benzoxazine (5.74 g), pyridine (1.9 g) and methylene chloride (100 ml) was dropwise added a solution of bromoacetyl bromide (5.82 g) in methylene chloride (5 ml) at room temperature. After the mixture was stirred for 1.0 hour at the same temperature, water (100 ml) was added thereto under stirring. The organic layer was separated, washed with water, dried over magnesium sulfate and evaporated. The residue was crystallized with a mixture of diisopropyl ether and ethyl acetate. The crystals were collected by filtration to give 4-bromoacetyl-5-benzoyl-3,4-dihydro-2H-1,4-benzoxazine (6.0 g).

Workup

  1. additionwas added
  2. customThe organic layer was separated
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue was crystallized with a mixture of diisopropyl ether and ethyl acetate
  7. filtrationThe crystals were collected by filtration

Sources & evidence

ORD record
ord-ff5b9e582f6b4c889545723eced11d76
Source dataset
uspto-grants-1995_03
Patent number
US05401737

Reaction notes

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