Ethyl Acetate → 7-Bromo-4-(thiazol-4-yl)coumarin

HRID 260445

Reaction equation

HRID 260445 reaction equation
[CH:1]([NH2:3])=[S:2].[Br:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9]([C:16](=O)[CH2:17]Br)=[CH:10][C:11](=[O:15])[O:12]2)=[CH:7][CH:6]=1.C(OCC)(=O)C>C1COCC1>[Br:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9]([C:16]3[N:3]=[CH:1][S:2][CH:17]=3)=[CH:10][C:11](=[O:15])[O:12]2)=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 3005587MethanethioamideHCID 233702397-bromo-4-(bromoacetyl)-2H-chromen-2-one

Product 1

HCID 194269437-Bromo-4-(thiazol-4-yl)coumarin

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Freshly prepared thioformamide (Helv. Chim. Acta, 31, 2065, 1948) (160 mg) was added to a solution of (α-bromoketone from Step 2 (200 mg) in THF (5 mL) and the reaction mixture was stirred at r.t. for 2 h. Ethyl acetate was then added and the organic phase was washed with saturated aqueous NH4Cl, H2O and brine, dried (MgSO4) and evaporated. Flash chromatography of the residue (silica gel; hexane/EtOAc (65:35) afforded the title compound as a white solid.

Workup

  1. washthe organic phase was washed with saturated aqueous NH4Cl, H2O and brine
  2. dry with materialdried (MgSO4)
  3. customevaporated

Sources & evidence

ORD record
ord-f263892467124d7491ef5fa10b99c9fb
Source dataset
uspto-grants-1996_06
Patent number
US05527827

Linked notes

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