p-Anisoyl chloride → HCID 9886338, compound

HRID 2288585Notes

Reaction equation

HRID 2288585 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:13]3[S:14][CH:15]=[CH:16][C:12]=3[CH2:11][CH2:10][NH:9]2)=[CH:4][CH:3]=1.[CH3:17][O:18][C:19]1[CH:27]=[CH:26][C:22]([C:23](Cl)=[O:24])=[CH:21][CH:20]=1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[C:13]3[S:14][CH:15]=[CH:16][C:12]=3[CH2:11][CH2:10][N:9]2[C:23]([C:22]2[CH:26]=[CH:27][C:19]([O:18][CH3:17])=[CH:20][CH:21]=2)=[O:24])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7477p-Anisoyl chlorideHCID 8471TriethylamineHCID 18699634HCID 18699634, compound

Product 1

HCID 9886338HCID 9886338, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

7-(4-Chloro-phenyl)-4,5,6,7-tetrahydrothieno[2,3-c]pyridin (100 mg) in toluene (20 ml), 4-methoxybenzoyl chloride (68.3 mg) and triethylamine (1 ml) were mixed and the mixture stirred at RT for 2 h. The reaction mixture was extracted once with NaOH (1 M) and once with water, the organic phase dried (MgSO4) and evaporated to dryness resulting in yellow oil which was purified on silica gel using methylene chloride/methanol 19/1 as eluent. The resulting oil was treated with abs ethanol resulting in precipitation of crystals. Yield 91%, m.p. 129.5-130.0 C. MS. M+=383.

Workup

  1. extractionThe reaction mixture was extracted once with NaOH (1 M) and once with water
  2. dry with materialthe organic phase dried (MgSO4)
  3. customevaporated to dryness
  4. customresulting in yellow oil which
  5. customwas purified on silica gel
  6. additionThe resulting oil was treated with abs ethanol resulting in precipitation of crystals

Sources & evidence

ORD record
ord-ef0b3deb5c2c417e812c25ff873d8406
Source dataset
uspto-grants-2000_07
Patent number
US06090797

Reaction notes

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