Thionyl Chloride → HCID 12018051, compound

HRID 2303382Notes

Reaction equation

HRID 2303382 reaction equation
Cl.[N:2]1([CH2:8][CH2:9][O:10][C:11]2[CH:19]=[CH:18][C:14]([C:15]([OH:17])=O)=[CH:13][C:12]=2[Cl:20])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.O=S(Cl)Cl.[CH3:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]2[S:37][C:36]3[CH:38]=[C:39]([O:42][CH3:43])[CH:40]=[CH:41][C:35]=3[CH:34]=2)=[CH:29][CH:28]=1.[Al+3].[Cl-].[Cl-].[Cl-]>ClCCl.CN(C=O)C>[CH3:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]2[S:37][C:36]3[CH:38]=[C:39]([O:42][CH3:43])[CH:40]=[CH:41][C:35]=3[C:34]=2[C:15]([C:14]2[CH:18]=[CH:19][C:11]([O:10][CH2:9][CH2:8][N:2]3[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]3)=[C:12]([Cl:20])[CH:13]=2)=[O:17])=[CH:29][CH:28]=1

Participants

7

Reactant 4

HCID 24386Thionyl ChlorideHCID 8509416-Methoxy-2-(4-methoxyphenyl)benzo[b]thiopheneHCID 6451240Aluminum(III) ChlorideHCID 69972363HCID 69972363, compound

Product 1

HCID 12018051HCID 12018051, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

2.6 g(8.12 mmol) of 4-[2-(1-piperidinyl)ethoxy]-3-chlorobenzoic acid hydrochloride was dissolved in 25 mL of dichloromethane and 50 mL of SOCl2 with three drops of DMF. The reaction was reluxed for sixteen hours under a nitrogen atmosphere. The reaction mixture was evaporated to dryness, then re-dissolved in 50 mL of dichloromethane. 2.2 g (8.12 mmol) of 2-(4-methoxyphenyl)-6-methoxybenzo[b]thiophene was added to the solution and cooled to 0° C. 7.6 g (56.8 mmol) of AlCl3 was added in three portions to the reaction mixture and allowed to proceed for 1.5 hours. The reaction was quenched by pouring into ice. The organic layer was separated and washed with Na2CO3 solution and with water. The organic layer was dried by filtration through Na2SO4 and evaporated to dryness. The crude material was chromatographed on a silica gel column (HPLC) with a linear gradient beginning with CHCl3 and ending with MeOH-CHCl3 (1:9). The desired fractions were determined by tlc, combined, and evaporated to dryness. This yielded 1.3 g of the title compound as a yellow amorphous foam. PMR: Consistent with the proposed structure

Workup

  1. waitThe reaction was reluxed for sixteen hours under a nitrogen atmosphere
  2. customThe reaction mixture was evaporated to dryness
  3. dissolutionre-dissolved in 50 mL of dichloromethane
  4. customThe reaction was quenched
  5. additionby pouring into ice
  6. customThe organic layer was separated
  7. washwashed with Na2CO3 solution and with water
  8. dry with materialThe organic layer was dried by filtration through Na2SO4
  9. customevaporated to dryness
  10. customThe crude material was chromatographed on a silica gel column (HPLC) with a linear gradient
  11. customevaporated to dryness

Sources & evidence

ORD record
ord-85c17c0fdbd64ed5a7e4fdaa906f52b4
Source dataset
uspto-grants-2002_08
Patent number
US06432982B1

Reaction notes

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