Water → Methyl 4-[(3-butyl-1-ethylthio-4-isoquinolinyl)-methyl]-benzoate

HRID 2260828

Reaction equation

HRID 2260828 reaction equation
[CH2:1]([S:3][C:4]#[N:5])[CH3:2].O=[C:7]([CH2:26][CH2:27][CH2:28][CH3:29])[CH:8]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:9][C:10]1[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:11]=1.O.[OH-].[NH4+]>P(Cl)(Cl)(Cl)=O>[CH2:26]([C:7]1[N:5]=[C:4]([S:3][CH2:1][CH3:2])[C:21]2[C:20]([C:8]=1[CH2:9][C:10]1[CH:11]=[CH:12][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:18][CH:19]=1)=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:27][CH2:28][CH3:29]

Participants

6

Reactant 4

HCID 962WaterHCID 10968Ethyl thiocyanateHCID 14923Ammonium HydroxideHCID 18999079Methyl 4-(3-oxo-2-phenyl-heptyl)-benzoate

Product 1

HCID 18999070Methyl 4-[(3-butyl-1-ethylthio-4-isoquinolinyl)-methyl]-benzoate

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

0.4 ml of ethyl thiocyanate and 0.45 ml of stannic chloride were added to a solution of 1 g of methyl 4-(3-oxo-2-phenyl-heptyl) benzoate of Step C in 20 ml of phosphorous oxychloride and the mixture was stirred for 10 hours at reflux, then poured into ice-cooled water. The mixture was stirred for 15 minutes and alkalized with concentrated ammonium hydroxide. Extraction was carried out with ethyl acetate and the extracts were washed with water, dried and evaporated to dryness. The residue was chromatographed on silica (eluant: hexane--ethyl acetate (9-1)) to obtain 0.57 g of the desired product melting at 70° C.

Workup

  1. temperatureat reflux
  2. additionpoured into ice-
  3. stirringThe mixture was stirred for 15 minutes
  4. extractionExtraction
  5. washthe extracts were washed with water
  6. customdried
  7. customevaporated to dryness
  8. customThe residue was chromatographed on silica (eluant: hexane--ethyl acetate (9-1))

Sources & evidence

ORD record
ord-64c9eeabc9384717812dd60ee6024c17
Source dataset
uspto-grants-1995_12
Patent number
US05478938

Linked notes

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