Boron tribromide → 2-(4-chlorophenyl)-6-hydroxy-4-methyl-2H-1,2,4-benzothiadiazine-3(4H)-one 1,1-dioxide

HRID 477880Notes

Reaction equation

HRID 477880 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:20]C)[CH:18]=[CH:19][C:10]=3[S:9]2(=[O:23])=[O:22])=[CH:4][CH:3]=1.B(Br)(Br)Br>C(Cl)Cl>[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:23])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 198725932-(4-chlorophenyl)-6-methoxy-4-methyl-2H-1,2,4-benzothiadiazine-3(4H)-one 1,1-dioxide

Product 1

HCID 198724772-(4-chlorophenyl)-6-hydroxy-4-methyl-2H-1,2,4-benzothiadiazine-3(4H)-one 1,1-dioxideYield 93.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(4-chlorophenyl)-6-methoxy-4-methyl-2H-1,2,4-benzothiadiazine-3(4H)-one 1,1-dioxide (21.0 g) in methylene chloride (200 ml) was added boron tribromide (1N solution in methylene chloride, 89.2 ml) at ambient temperature. The mixture was stirred for 8 hours at the same temperature and then poured into ice water. The separated solid was collected by filtration, dried, and recrystallized from ethanol to yield 2-(4-chlorophenyl)-6-hydroxy-4-methyl-2H-1,2,4-benzothiadiazine-3(4H)-one 1,1-dioxide (18.86 g).

Workup

  1. filtrationThe separated solid was collected by filtration
  2. customdried
  3. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-5be268f928fe451b98401e247381e819
Source dataset
uspto-grants-1989_12
Patent number
US04889851

Reaction notes

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