Dimethylformamide → HCID 86688840, compound

HRID 2275395Notes

Reaction equation

HRID 2275395 reaction equation
[CH2:1]([N:7]1[C:11]([C:12]2[S:19][C:18]3[CH:17]=[CH:16][S:15][C:14]=3[CH:13]=2)=[CH:10][CH:9]=[C:8]1[C:20]1[S:27][C:26]2[CH:25]=[CH:24][S:23][C:22]=2[CH:21]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].P(Cl)(Cl)(Cl)=O.CN([CH:36]=[O:37])C.[C:38](=O)([O-])[OH:39].[Na+]>ClCCl>[CH:38]([C:24]1[S:23][C:22]2[CH:21]=[C:20]([C:8]3[N:7]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[C:11]([C:12]4[S:19][C:18]5[CH:17]=[C:16]([CH:36]=[O:37])[S:15][C:14]=5[CH:13]=4)=[CH:10][CH:9]=3)[S:27][C:26]=2[CH:25]=1)=[O:39]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 86688841HCID 86688841, compound

Product 1

HCID 86688840HCID 86688840, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-hexyl-2,5-bis(thieno[3,2-b]thiophen-5-yl)pyrrole (74) in dichloromethane is added a solution of phosphorus oxychloride and DMF in DCM. The reaction mixture is refluxed for 16 h, then sat. sodium hydrogencarbonate solution 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 the product.

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
  6. customto obtain the product

Sources & evidence

ORD record
ord-42a9e854814e4688990ab929d6ccdb4e
Source dataset
uspto-grants-2015_09
Patent number
US09127020B2

Reaction notes

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