Boron tribromide → 3-benzyl-5-{[N-(4-hydroxyphenyl)-methylamino]-methylene}-2-thioxothiazolidin-4-one

HRID 600827Notes

Reaction equation

HRID 600827 reaction equation
[CH2:1]([N:8]1[C:12](=[O:13])[C:11](=[CH:14][N:15]([CH3:24])[C:16]2[CH:21]=[CH:20][C:19]([O:22]C)=[CH:18][CH:17]=2)[S:10][C:9]1=[S:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(Br)(Br)Br>C(Cl)Cl>[CH2:1]([N:8]1[C:12](=[O:13])[C:11](=[CH:14][N:15]([CH3:24])[C:16]2[CH:17]=[CH:18][C:19]([OH:22])=[CH:20][CH:21]=2)[S:10][C:9]1=[S:25])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 723711863-benzyl-5-{[N-(4-methoxyphenyl)-methylamino]-methylene}-2-thioxothiazolidin-4-one

Product 1

HCID 866204233-benzyl-5-{[N-(4-hydroxyphenyl)-methylamino]-methylene}-2-thioxothiazolidin-4-oneYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 3-benzyl-5-{[N-(4-methoxyphenyl)-methylamino]-methylene}-2-thioxothiazolidin-4-one (0.25 g, 0.67 mmol) in DCM (6 mL, anhyd) chilled to −78° C. was added dropwise a 1.0 M solution of boron tribromide in DCM (4.0 mL, 4.0 mmol). The reaction flask was removed from the dry-ice bath and allowed to warm to ambient temperature. After 4 h the reaction flask was chilled again to −78° C., and the reaction mixture was quenched by addition of MeOH (30 mL). The reaction mixture then was concentrated under reduced pressure and chromatographed (silica gel, DCM) to afford 3-benzyl-5-{[N-(4-hydroxyphenyl)-methylamino]-methylene}-2-thioxothiazolidin-4-one (0.16 g, 67%) as a yellow solid. 1H-NMR (CDCl3): δ 7.73 (1H, s), 7.44 (2H, d), 7.23-7.31 (3H, m), 7.07 (2H, m), 6.89 (2H, m), 5.30 (1H, s), 5.24 (2H, s), 3.49 (3H, s).

Workup

  1. customThe reaction flask was removed from the dry-ice bath
  2. temperatureAfter 4 h the reaction flask was chilled again to −78° C.
  3. customthe reaction mixture was quenched by addition of MeOH (30 mL)
  4. concentrationThe reaction mixture then was concentrated under reduced pressure
  5. customchromatographed (silica gel, DCM)

Sources & evidence

ORD record
ord-27ef68611dd24d028c032722501795f6
Source dataset
uspto-grants-2011_03
Patent number
US07902237B2

Reaction notes

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