Phosgene → 6-[4-(Benzenesulfinyl)butoxy]-1,4-dihydro-2H-3,1-benzoxazin-2-one

HRID 463217Notes

Reaction equation

HRID 463217 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][S:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:16])=[CH:6][C:3]=1[CH2:4][OH:5].[C:23](=O)([O-])[O-:24].[K+].[K+].C(Cl)(Cl)=O>C(Cl)(Cl)Cl.C1(C)C=CC=CC=1>[C:17]1([S:15]([CH2:14][CH2:13][CH2:12][CH2:11][O:10][C:7]2[CH:8]=[CH:9][C:2]3[NH:1][C:23](=[O:24])[O:5][CH2:4][C:3]=3[CH:6]=2)=[O:16])[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 3

HCID 6371PhosgeneHCID 11430Potassium CarbonateHCID 566193032-Amino-5-(4-phenylsulfinylbutoxy)-benzyl alcohol

Product 1

HCID 132605746-[4-(Benzenesulfinyl)butoxy]-1,4-dihydro-2H-3,1-benzoxazin-2-one

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6212ChloroformSolvent

Procedure

An amount of 4.2 gm (0.0133 mol) of 2-amino-5-(4-phenylsulfinylbutoxy)-benzyl alcohol [prepared from 2-nitro-5-(4-phenylsulfinyl-butoxy)-benzyl alcohol by catalytic hydrogenation] is dissolved in 150 ml of chloroform and mixed with 6.9 gm (0.05 mol) of potassium carbonate. Ten milliliters of a 20% solution of phosgene in toluene is slowly added dropwise to this mixture under stirring. After further stirring for two hours, the solution is washed with water and dried with sodium sulfate, and the solvents are distilled off in vacuo. The residue is recrystallized from ethyl acetate/cyclohexane.

Workup

  1. stirringAfter further stirring for two hours
  2. washthe solution is washed with water
  3. dry with materialdried with sodium sulfate
  4. distillationthe solvents are distilled off in vacuo
  5. customThe residue is recrystallized from ethyl acetate/cyclohexane

Sources & evidence

ORD record
ord-f272e97895fb498895b36de5ac28fbe3
Source dataset
uspto-grants-1985_05
Patent number
US04518597

Reaction notes

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