Thionyl Chloride → 6-(4-Chlorobutoxy)-1,4-dihydro-2H-3,1-benzoxazin-2-one

HRID 463064Notes

Reaction equation

HRID 463064 reaction equation
O[CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]2[NH:15][C:14](=[O:16])[O:13][CH2:12][C:11]=2[CH:17]=1.S(Cl)([Cl:20])=O>N1C=CC=CC=1>[Cl:20][CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]2[NH:15][C:14](=[O:16])[O:13][CH2:12][C:11]=2[CH:17]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 132605006-(4-Hydroxybutoxy)-1,4-dihydro-2H-3,1-benzoxazin-2-one

Product 1

HCID 132605016-(4-Chlorobutoxy)-1,4-dihydro-2H-3,1-benzoxazin-2-one

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Sixty grams (0.253 mol) of 6-(4-hydroxy-butoxy)-4H-3,1-benzoxazin-2-one and 5 ml of pyridine are added to 300 ml of thionyl chloride, under stirring, at ambient temperature. After refluxing for two hours, the excess thionyl chloride is distilled off in a rotary evaporator, and the residue is taken up in chloroform and is stirred with the same volume of ice water for 30 minutes. Then, the chloroform phase is removed, washed twice with water, and dried with sodium sulfate, and the chloroform is distilled off. The residue is recrystallized from toluene/diisopropylether (3:1).

Workup

  1. temperatureAfter refluxing for two hours
  2. distillationthe excess thionyl chloride is distilled off in a rotary evaporator
  3. stirringis stirred with the same volume of ice water for 30 minutes
  4. customThen, the chloroform phase is removed
  5. washwashed twice with water
  6. dry with materialdried with sodium sulfate
  7. distillationthe chloroform is distilled off
  8. customThe residue is recrystallized from toluene/diisopropylether (3:1)

Sources & evidence

ORD record
ord-4343e02bf38e4b06915b203529f158db
Source dataset
uspto-grants-1985_05
Patent number
US04518597

Reaction notes

Loading…