Benzoyl chloride → HCID 72334349, compound

HRID 2261144Notes

Reaction equation

HRID 2261144 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([CH:11]=[C:12]3[S:16][C:15](=[O:17])[NH:14][C:13]3=[O:18])=[CH:10][C:5]=2[NH:4][CH2:3][CH2:2]1.[C:19](Cl)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.CCN(C(C)C)C(C)C.CCOC(C)=O>C1COCC1>[C:19]([N:4]1[C:5]2[CH:10]=[C:9]([CH:11]=[C:12]3[S:16][C:15](=[O:17])[NH:14][C:13]3=[O:18])[CH:8]=[CH:7][C:6]=2[O:1][CH2:2][CH2:3]1)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 7412Benzoyl chloride2×HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 72334357HCID 72334357, compound

Product 1

HCID 72334349HCID 72334349, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-(3,4-Dihydro-2H-benzo[1,4]oxazin-6-ylmethylene)-thiazolidine-2,4-dione (example 96) (35 mg, 0.13 mmol) in 4 ml anhydrous THF were treated with benzoylchloride (156 uL, 10 eq.) in the presence of DIEA (2 eq.) for 3 h. Excess of benzoylchloride was hydrolysed, EtOAc was added and the organic phase was washed with NaHCO3 and brine. The crude was purified on silica gel using EtOAc/cyclohexane 3:7 as eluent affording 14 mg (35%) of the title compound.

Workup

  1. washthe organic phase was washed with NaHCO3 and brine
  2. customThe crude was purified on silica gel

Sources & evidence

ORD record
ord-7dcda5d1d5ec41119bc91ff4bbf40705
Source dataset
uspto-grants-2010_12
Patent number
US07846925B2

Reaction notes

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