Potassium Carbonate → 2-(4-chlorophenyl)-4-methyl-6-cyclohexylmethoxy-2H-1,2,4-benzothiadiazine-3(4H)-one 1,1-dioxide

HRID 477884Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[N:12]([CH3:15])[C:11]3[CH:16]=[C:17](O)[CH:18]=[CH:19][C:10]=3[S:9]2(=[O:22])=[O:21])=[CH:4][CH:3]=1.[C:23](=[O:26])([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[N:12]([CH3:15])[C:11]3[CH:16]=[C:17]([O:26][CH2:23][CH:2]4[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]4)[CH:18]=[CH:19][C:10]=3[S:9]2(=[O:22])=[O:21])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A suspension of 2-(4-chlorophenyl)-6-hydroxy-4-methyl-2H-1,2,4-benzothiadiazine-3(4H)-one 1,1-dioxide (250 mg), potassium carbonate (122 mg) and bromomethylyclohexane (159 mg) in N,N-dimethyl formamide (1 ml) was stirred for 2 hours at 60° C. The mixture was poured into ice water. The separator solid was collected by filtration, dried, and recrystallized from ethanol to yield 2-(4-chlorophenyl)-4-methyl-6-cyclohexylmethoxy-2H-1,2,4-benzothiadiazine-3(4H)-one 1,1-dioxide (230 mg).

Workup

filtrationThe separator solid was collected by filtration
customdried
customrecrystallized from ethanol

Sources & evidence

ORD record: ord-4b9f0aef0d2e419897a700f808aaca23
Source dataset: uspto-grants-1989_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04889851

Reaction notes

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