Dimethylformamide → HCID 86688836, compound

HRID 2275390Notes

Reaction equation

HRID 2275390 reaction equation
[CH2:1]([C:5]1[CH:9]=[CH:8][S:7][C:6]=1[C:10]1[S:11][C:12]2[C:13](=[CH:15][CH:16]=[C:17]3[C:25]4[S:24][C:23]([C:26]5[S:27][CH:28]=[CH:29][C:30]=5[CH2:31][CH2:32][CH2:33][CH3:34])=[CH:22][C:21]=4[CH:20]=[CH:19][C:18]=23)[CH:14]=1)[CH2:2][CH2:3][CH3:4].P(Cl)(Cl)(Cl)=O.CN([CH:43]=[O:44])C.[C:45](=O)([O-])[OH:46].[Na+]>ClCCl>[CH2:1]([C:5]1[CH:9]=[C:8]([CH:43]=[O:44])[S:7][C:6]=1[C:10]1[S:11][C:12]2[C:18]3=[CH:19][CH:20]=[C:21]4[C:25]([S:24][C:23]([C:26]5[S:27][C:28]([CH:45]=[O:46])=[CH:29][C:30]=5[CH2:31][CH2:32][CH2:33][CH3:34])=[CH:22]4)=[C:17]3[CH:16]=[CH:15][C:13]=2[CH:14]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 70653257HCID 70653257, compound

Product 1

HCID 86688836HCID 86688836, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of benzothiophenobenzothiophene 20 (300 mg, 0.58 mmol) in 7 ml of dichloromethane is added a solution of 1.1 ml (11.4 mmol) of phosphorus oxychloride and 0.94 ml (12.2 mmol) of DMF in 7 ml of DCM. The reaction mixture is refluxed for 16 h, then sat. sodium hydrogencarbonate solution (50 ml) is added and the mixture is stirred at room temperature for 2 h. After phase separation, the organic phase is dried over sodium sulfate. After the solvents have been distilled off, the residue is recrystallized from toluene to obtain 172 mg (52%) of product. 1H NMR (TCE-d2, 375 K): 9.83 ppm (s, 2H), 8.01 (d, 2H), 7.90 (s, 2H), 7.61 (s, 4H), 2.92 (dd, 4H), 1.72 (m, 4H), 1.44 (qa, 4H), 0.95 (t, 6H).

Workup

  1. temperatureThe reaction mixture is refluxed for 16 h
  2. customAfter phase separation
  3. dry with materialthe organic phase is dried over sodium sulfate
  4. distillationAfter the solvents have been distilled off
  5. customthe residue is recrystallized from toluene

Sources & evidence

ORD record
ord-4821a6fc4c794927aab01823cc40ec6f
Source dataset
uspto-grants-2015_09
Patent number
US09127020B2

Reaction notes

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