Boron tribromide → HCID 19854838, compound

HRID 34335Notes

Reaction equation

HRID 34335 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 600 ml 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-46295ae8758b4beebe3c52e3f8d6ade3
Source dataset
uspto-grants-1988_08
Patent number
US04761424

Reaction notes

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