Sodium Hydroxide → HCID 67177333, compound

HRID 1676962Notes

Reaction equation

HRID 1676962 reaction equation
C[O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][C:7]([S:10][CH2:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)=[CH:6][CH:5]=1.[OH-].[Na+:22]>O1CCCC1.CO>[Na+:22].[N:17]1[CH:16]=[CH:15][C:14]([CH2:13][CH2:12][CH2:11][S:10][C:7]2[CH:6]=[CH:5][C:4]([C:3]([O-:20])=[O:2])=[CH:9][CH:8]=2)=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67177770Methyl 4-{[3-(pyridin-4-yl)propyl]sulfanyl}benzoate2×

Product 1

HCID 67177333HCID 67177333, compoundYield 100.7%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Heat a stirring solution of 4-(3-pyridin-4-yl-propylsulfanyl)-benzoic acid methyl ester (174 mg, 0.605 mmol) (Intermediate 10) and 2N sodium hydroxide (0.42 mL, 0.848 mmol) in 1:1 tetrahydrofuran/methanol (4 ml) to reflux temperature for 18 h. The reaction is allowed to cool and then concentrated in vacuo to obtain 180 mg (99%) of the title compound. MS (ES+) m/e 274.0 (M+1)+.

Workup

  1. temperatureto reflux temperature for 18 h
  2. temperatureto cool
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-32f8d9ce447e4d1bb048f7a477ce3fff
Source dataset
uspto-grants-2011_08
Patent number
US08008296B2

Reaction notes

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