Water → 2-(4-chlorophenyl)-6-[1-(ethoxycarbonyl)ethoxyl]-4-methyl-2H-1,2,4-benzothiadiazine-3(4H)-one 1,1-dioxide

HRID 477886Notes

Reaction equation

HRID 477886 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]([OH:20])[CH:18]=[CH:19][C:10]=3[S:9]2(=[O:22])=[O:21])=[CH:4][CH:3]=1.Br[CH:24]([CH3:30])[C:25]([O:27][CH2:28][CH3:29])=[O:26].C(=O)([O-])[O-].[K+].[K+].O>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:20][CH:24]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH3:30])[CH:18]=[CH:19][C:10]=3[S:9]2(=[O:21])=[O:22])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 79040Ethyl 2-bromopropionateHCID 198724772-(4-chlorophenyl)-6-hydroxy-4-methyl-2H-1,2,4-benzothiadiazine-3(4H)-one 1,1-dioxide

Product 1

HCID 198724672-(4-chlorophenyl)-6-[1-(ethoxycarbonyl)ethoxyl]-4-methyl-2H-1,2,4-benzothiadiazine-3(4H)-one 1,1-dioxideYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-(4-chlorophenyl)-6-hydroxy-4-methyl-2H-1,2,4-benzothiadiazine-3(4H)-one 1,1-dioxide (678 mg), ethyl 2-bromopropionate (362 mg), and potassium carbonate (207 mg) in dry N,N-dimethyl formamide (2 ml) was stirred overnight at ambient temperature. The mixture was poured into water and extracted twice with ethyl acetate. The organic layers were washed with water, dried, and evaporated under reduced pressure. The residue was crystallized from n-hexane to yield 2-(4-chlorophenyl)-6-[1-(ethoxycarbonyl)ethoxy]-4-methyl-2H-1,2,4-benzothiadiazine -3(4H)-one 1,1-dioxide (816 mg). (R,S mixture)

Workup

  1. extractionextracted twice with ethyl acetate
  2. washThe organic layers were washed with water
  3. customdried
  4. customevaporated under reduced pressure
  5. customThe residue was crystallized from n-hexane

Sources & evidence

ORD record
ord-62b26d76537944458593de93c50f0bcb
Source dataset
uspto-grants-1989_12
Patent number
US04889851

Reaction notes

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