Potassium Carbonate → 6-[4-(3,4-Dichloro-phenylsulfinyl)-butoxy]-4,4-dimethyl-4H-3,1-benzoxazin-2-one
Reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:10][C:9](=[O:11])[O:8][C:7]([CH3:13])([CH3:12])[C:6]=2[CH:14]=1.[Cl:15][C:16]1[CH:17]=[C:18]([S:23]([CH2:25][CH2:26][CH2:27][CH2:28]Br)=[O:24])[CH:19]=[CH:20][C:21]=1[Cl:22].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[Cl:15][C:16]1[CH:17]=[C:18]([S:23]([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][C:7]([CH3:12])([CH3:13])[C:6]=3[CH:14]=2)=[O:24])[CH:19]=[CH:20][C:21]=1[Cl:22]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 40 °C
Procedure
A solution of 1.9 gm (0.01 mol) of 6-hydroxy-4,4-dimethyl-4H-3,1-benzoxazin-2-one and 4.1 gm (0.0125 mol) of 4-(3,4-dichlorophenyl-sulfinyl)-butylbromide (m.p.: 63°-64° C.) in 40 ml of dimethylsulfoxide is mixed with 3.5 gm (0.025 mol) of potassium carbonate, and the mixture is stirred for three hours at 40° C. After cooling, copious amounts of ice water are added, and the mixture is extracted with chloroform. The extract is washed with water and dried with sodium sulfate, and the chloroform is distilled off. The residue is recrystallized from isopropanol/diisopropylether.
Workup
- temperatureAfter cooling
- extractionthe mixture is extracted with chloroform
- washThe extract is washed with water
- dry with materialdried with sodium sulfate
- distillationthe chloroform is distilled off
- customThe residue is recrystallized from isopropanol/diisopropylether
Sources & evidence
- ORD record
- ord-0d70346763624095a825da169f61e3c6
- Source dataset
- uspto-grants-1985_05
- Patent number
- US04518597
Reaction notes
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