Water → 3-(2-Bromopropanoyl)spiro[benzo[e][1,3]oxazine-2,1'-cyclohexan]-4(3H)-one

HRID 849305Notes

Reaction equation

HRID 849305 reaction equation
[Br:1][CH:2]([CH3:6])[C:3](Br)=[O:4].N1C=CC=CC=1.[C:13]12([NH:23][C:22](=[O:24])[C:21]3[CH:25]=[CH:26][CH:27]=[CH:28][C:20]=3[O:19]1)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2.O>C(Cl)Cl>[Br:1][CH:2]([CH3:6])[C:3]([N:23]1[C:13]2([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]2)[O:19][C:20]2[CH:28]=[CH:27][CH:26]=[CH:25][C:21]=2[C:22]1=[O:24])=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 79047Propanoyl bromide, 2-bromo-HCID 652743spiro[benzo[e][1,3]oxazine-2,1'-cyclohexan]-4(3H)-one

Product 1

HCID 103380523-(2-Bromopropanoyl)spiro[benzo[e][1,3]oxazine-2,1'-cyclohexan]-4(3H)-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of 89.1 ml of 2-bromopropionyl bromide in 95 ml of methylene chloride and a solution of 61.13 g of pyridine in 95 ml of methylene chloride are added dropwise to a suspension of 140 g of spiro[2,3-dihydro-4H-1,3-benzoxazine-2,1'-cyclohexan]-4-one in 190 ml of methylene chloride under nitrogen atmosphere at -5° C. during about 45 minutes. Then the mixture is stirred at a room temperature for 6 hours. The reaction mixture is poured into 500 ml of water and the mixture is extracted with methylene chloride. The extract is washed, dried and evaporated to remove the solvent and the residue obtained is crystallized from methanol and the crystals are collected by filtration to obtain 197.3 g of 3-(2-bromopropionyl)-spiro[2,3-dihydro-4H-1,3-benzoxazine-2,1'-cyclohexan]-4-one.

Workup

  1. extractionthe mixture is extracted with methylene chloride
  2. washThe extract is washed
  3. customdried
  4. customevaporated
  5. customto remove the solvent
  6. customthe residue obtained
  7. customis crystallized from methanol
  8. filtrationthe crystals are collected by filtration

Sources & evidence

ORD record
ord-36acb39e23254159b836ce323c3ea95e
Source dataset
uspto-grants-2000_01
Patent number
US06011150

Reaction notes

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