Dimethyl Sulfoxide → 6-[4-(4-Bromo-phenylmercapto)-butoxy]-4,4-dimethyl-4H-3,1-benzoxazin-2-one

HRID 463070Notes

Reaction equation

HRID 463070 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].CS(C)=O.Cl[CH2:20][CH2:21][CH2:22][CH2:23][O:24][C:25]1[CH:26]=[CH:27][C:28]2[NH:33][C:32](=[O:34])[O:31][C:30]([CH3:36])([CH3:35])[C:29]=2[CH:37]=1>O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:20][CH2:21][CH2:22][CH2:23][O:24][C:25]2[CH:26]=[CH:27][C:28]3[NH:33][C:32](=[O:34])[O:31][C:30]([CH3:36])([CH3:35])[C:29]=3[CH:37]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 660494-BromothiophenolHCID 132605036-(4-Chlorobutoxy)-4,4-dimethyl-1,4-dihydro-2H-3,1-benzoxazin-2-one

Product 1

HCID 132605086-[4-(4-Bromo-phenylmercapto)-butoxy]-4,4-dimethyl-4H-3,1-benzoxazin-2-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Quantities of 6.23 gm (0.033 mol) of 4-bromothiophenol and 8.28 gm (0.06 mol) of potassium carbonate are stirred into 100 ml of dimethylsulfoxide, dried over a molecular sieve in a nitrogen atmosphere at ambient temperature for 15 minutes, and then mixed with 8.51 gm (0.03 mol) of 6-(4-chlorobutoxy)-4,4-dimethyl-4H-3,1-benzoxazin-2-one. After stirring for one hour at ambient temperature, water is added in batches until a thick crystal slurry is produced. This is subjected to suction filtration, dried, and recrystallized from ethyl acetate/diisopropyl ether.

Workup

  1. customdried over a molecular sieve in a nitrogen atmosphere at ambient temperature for 15 minutes
  2. customis produced
  3. filtrationThis is subjected to suction filtration
  4. customdried
  5. customrecrystallized from ethyl acetate/diisopropyl ether

Sources & evidence

ORD record
ord-fb115217563a4aa2bf2f76a04a13f1ce
Source dataset
uspto-grants-1985_05
Patent number
US04518597

Reaction notes

Loading…