Boron tribromide → HCID 19854838, compound

HRID 1607923Notes

Reaction equation

HRID 1607923 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:19]([CH:21]3[C:26](=[O:27])[C:25]4[CH:28]=[CH:29][CH:30]=[CH:31][C:24]=4[S:23][CH2:22]3)=[O:20])=[CH:14][CH:13]=2)[CH:6]=[CH:7][C:8]=1[O:9]C.B(Br)(Br)Br>ClCCl>[OH:2][C:3]1[CH:4]=[C:5]([CH2:11][C:12]2[CH:13]=[CH:14][C:15]([NH:18][C:19]([CH:21]3[C:26](=[O:27])[C:25]4[CH:28]=[CH:29][CH:30]=[CH:31][C:24]=4[S:23][CH2:22]3)=[O:20])=[CH:16][CH:17]=2)[CH:6]=[CH:7][C:8]=1[OH:9]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 19854843N-[4-[(3,4-dimethoxyphenyl)methyl]phenyl]-3,4-dihydro-4-oxo-2H-1-benzothiopyran-3-carboxamide

Product 1

HCID 19854838HCID 19854838, compoundYield 63.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of 1.0 g (2.1 mmol) of N-[4-[(3,4-dimethoxyphenyl)methyl]phenyl]-3,4-dihydro-4-oxo-2H-1-benzothiopyran-3-carboxamide, 1,1-dioxide and BBr3.S (CH3)2 (4.0 g, 12.6 mmol) in 150 ml of dichloromethane was heated under reflux under nitrogen for 18 hours. The resulting yellow suspension was poured onto 600ml of ice water, stirred for one and one-half hours and then filtered. The crude product was recrystallized from isopropanol-water to yield 544 mg (59%) of N-[4-[(3,4-dihydroxyphenyl)methyl]phenyl]-3,4-dihydro-4-oxo-2H-1-benzothiopyran-3-carboxamide, 1,1-dioxide, mp 216°-218° C.

Workup

  1. temperatureunder reflux under nitrogen for 18 hours
  2. filtrationfiltered
  3. customThe crude product was recrystallized from isopropanol-water

Sources & evidence

ORD record
ord-cb883c07bc5342408e6502de74ac145c
Source dataset
uspto-grants-1989_09
Patent number
US04868200

Reaction notes

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