Dimethylformamide → HCID 54268796, compound

HRID 1873148Notes

Reaction equation

HRID 1873148 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:18]4[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][C:19]=4[S:20][C:16]=3[CH:15]=[C:14]3[C:9]=2[CH:10]=[CH:11][CH:12]=[CH:13]3)=[CH:4][CH:3]=1.Br[CH2:27][C:28]([O:30][CH3:31])=[O:29].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH3:31][O:30][C:28](=[O:29])[CH2:27][O:25][C:22]1[CH:23]=[CH:24][C:18]2[C:17]3[C:8]([C:5]4[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][CH:4]=4)=[C:9]4[C:14](=[CH:15][C:16]=3[S:20][C:19]=2[CH:21]=1)[CH:13]=[CH:12][CH:11]=[CH:10]4

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 1548123611-(4-Hydroxy-phenyl)-benzo[b]naphtho[2,3-d]thiophen-3-ol

Product 1

HCID 54268796HCID 54268796, compoundYield 58.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

11-(4-Hydroxy-phenyl)-benzo[b]naphtho[2,3-d]thiophen-3-ol (1.36 g, 3.96 mmol), methyl bromoacetate (0.38 mL, 4.01 mmol), potassium carbonate (0.548 g, 3.97 mmol) and N,N-dimethylformamide (21 mL) were combined and stirred at ambient temperatures for 2.5 h. The reaction mixture was added to water and extracted with ethyl acetate and THF. Silica gel was added to the organic phase and the solvent was removed. The adsorbate was flash chromatographed (eluent:gradient dichloromethane to 98:2 dichloromethane:acetonitrile) to provide the title compound as a white solid (0.953 g, 58%): mp: 229-231° C: NMR (DMSO-d6); δ9.78 (s, 1 H), 8.51 (s, 1 H), 8.00 (d, J=8 Hz, 1 H), 7.56-7.39 (m, 4 H), 7.18 (d, J=9 Hz, 2 H), 7.05 (d, J=9 Hz, 2 H), 6.79 (dd, J=9, 2 Hz, 1 H), 6.66 (d, J=9 Hz, 1 H), 4.86 (s, 2 H), 3.68 (s, 3 H); MS (EI): 414 (100%, M+); Anal. Calc. for C25 H18O4S: C, 72.45, H, 4.38, N, 0.00. Found: C, 71.78, H, 4.41, N, 0.13.

Workup

  1. extractionextracted with ethyl acetate and THF
  2. additionSilica gel was added to the organic phase
  3. customthe solvent was removed
  4. customchromatographed (eluent:gradient dichloromethane to 98:2 dichloromethane:acetonitrile)

Sources & evidence

ORD record
ord-543dc78195804bfdbf34a1d6469d4e36
Source dataset
uspto-grants-2000_08
Patent number
US06110962

Reaction notes

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