Ethanethiol → HCID 12992516, compound

HRID 354080Notes

Reaction equation

HRID 354080 reaction equation
C[O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH:10]=[C:9]([C:11]3[CH:19]=[CH:18][C:14]4[N:15]=[CH:16][S:17][C:13]=4[CH:12]=3)[S:8][C:7]=2[CH:20]=1.[N:21]1([CH2:27][CH2:28][O:29][C:30]2[CH:38]=[CH:37][C:33]([C:34](Cl)=[O:35])=[CH:32][CH:31]=2)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.[Al+3].[Cl-].[Cl-].[Cl-].C(S)C>C(Cl)Cl>[S:17]1[C:13]2[CH:12]=[C:11]([C:9]3[S:8][C:7]4[CH:20]=[C:3]([OH:2])[CH:4]=[CH:5][C:6]=4[C:10]=3[C:34]([C:33]3[CH:32]=[CH:31][C:30]([O:29][CH2:28][CH2:27][N:21]4[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]4)=[CH:38][CH:37]=3)=[O:35])[CH:19]=[CH:18][C:14]=2[N:15]=[CH:16]1

Participants

6

Reactant 4

HCID 6343EthanethiolHCID 6451240Aluminum(III) ChlorideHCID 111190664-(2-(Piperidin-1-yl)ethoxy)benzoyl chlorideHCID 12992515HCID 12992515, compound

Product 1

HCID 12992516HCID 12992516, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the product from Example 18, Step 2 (63 mg, 0.21 mmol) and 4-(2-Piperidin-1-yl-ethoxy)-benzoyl chloride (1.38 mL, 0.25 mmol) in 1 mL of methylene chloride was added AlCl3 (212 mg, 1.6 mmol) and the reaction was stirred at room temperature for 3 hrs. When acylation was complete, to demethylate, ethanethiol (0.069 mL, 0.93 mmol) was added dropwise and the reaction stirred for a further 1.5 hrs. The reaction was cooled to 0° C. and quenched with saturated sodium bicarbonate solution. The organic layer was separated and the aqueous layer was extracted with 10% MeOH/methylene chloride. The organic layers were combined, dried over anhydrous sodium sulfate, filtered, and concentrated. The crude product was chromatographed on silica gel using 2% MeOH/methylene chloride to 4% MeOH/methylene chloride as the gradient eluant to obtain the title product.

Workup

  1. stirringthe reaction stirred for a further 1.5 hrs
  2. temperatureThe reaction was cooled to 0° C.
  3. customquenched with saturated sodium bicarbonate solution
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with 10% MeOH/methylene chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product was chromatographed on silica gel using 2% MeOH/methylene chloride to 4% MeOH/methylene chloride as the gradient eluant

Sources & evidence

ORD record
ord-0f092e8b8beb42e1b43940ef6cb5c58e
Source dataset
uspto-grants-2004_06
Patent number
US06756388B1

Reaction notes

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