Sodium ethoxide → 6-[4-(Phenylsulfanyl)butoxy]-1,4-dihydro-2H-3,1-benzoxazin-2-one

HRID 463073Notes

Reaction equation

HRID 463073 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:10][C:9](=[O:11])[O:8][CH2:7][C:6]=2[CH:12]=1.[O-]CC.[Na+].[Na].[C:18]1([S:24][CH2:25][CH2:26][CH2:27][CH2:28]Br)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(O)C>[C:18]1([S:24][CH2:25][CH2:26][CH2:27][CH2:28][O:1][C:2]2[CH:3]=[CH:4][C:5]3[NH:10][C:9](=[O:11])[O:8][CH2:7][C:6]=3[CH:12]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 111841484-Phenylmercapto-butylbromideHCID 132604846-hydroxy-2,4-dihydro-1H-3,1-benzoxazin-2-one

Product 1

HCID 202817246-[4-(Phenylsulfanyl)butoxy]-1,4-dihydro-2H-3,1-benzoxazin-2-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

An amount of 4.95 gm (0.03 mol) of 6-hydroxy-4H-3,1-benzoxazin-2-one is added to an ethanolic sodium ethoxide solution prepared from 150 ml of ethanol and 0.92 gm (9.04 mol) of sodium, and the mixture is refluxed. Ten grams (0.04 mol) of 4-phenylmercapto-butylbromide (prepared from thiophenol and excess 1,4-di-bromo-butane, Bp 0.03 mb :=95°-104° C.) are added to the hot solution, and the mixture is refluxed for a further two hours. After cooling, the reaction solution is poured onto ice water and extracted with ethyl acetate. The extract is washed with water and dried with sodium sulfate, and the ethyl acetate is distilled off in vacuo. The residue is recrystallized from cyclohexane/ethyl acetate.

Workup

  1. temperaturethe mixture is refluxed
  2. temperaturethe mixture is refluxed for a further two hours
  3. temperatureAfter cooling
  4. additionthe reaction solution is poured onto ice water
  5. extractionextracted with ethyl acetate
  6. washThe extract is washed with water
  7. dry with materialdried with sodium sulfate
  8. distillationthe ethyl acetate is distilled off in vacuo
  9. customThe residue is recrystallized from cyclohexane/ethyl acetate

Sources & evidence

ORD record
ord-b01a03ff20b040139372a7c82e8065b6
Source dataset
uspto-grants-1985_05
Patent number
US04518597

Reaction notes

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