2-Naphthalenesulfonic acid → HCID 19691974, compound

HRID 1631

Reaction equation

HRID 1631 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][NH:5][CH2:6]2.CS[C:13]1[S:14][CH2:15][CH2:16][N:17]=1.C1C2C(=CC=CC=2)C=CC=1S(O)(=O)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][N:5]([C:13]1[S:14][CH2:15][CH2:16][N:17]=1)[CH2:6]2

Participants

5

Reactant 3

HCID 84202-Naphthalenesulfonic acidHCID 883244,5-Dihydro-2-(methylthio)thiazoleHCID 147958684-Chloro-2,3-dihydro-1H-isoindole

Product 1

HCID 19691974HCID 19691974, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 4-chloroisoindoline (700 mg), 2-methylthio-2-thiazoline (600 mg), and β-naphthylsulfonic acid (35 mg) was heated at 150° C. for 30 minutes. The product was cooled, dissolved in methylene chloride, washed with water, the organic layer dried over anhydrous potassium carbonate, filtered, and solvent removed from the filtrate under reduced pressure. The residue was chromatographed on silica gel packed in methylene chloride/2% methanol/ammonia, eluting with methylene chloride/2% methanol, to give 4-chloro-2-(thiazolin-2-yl)isoindoline, a compound of Formula (IA), m.p. 167°-169° C.

Workup

  1. temperatureThe product was cooled
  2. washwashed with water
  3. dry with materialthe organic layer dried over anhydrous potassium carbonate
  4. filtrationfiltered
  5. customsolvent removed from the filtrate under reduced pressure
  6. customThe residue was chromatographed on silica gel
  7. washeluting with methylene chloride/2% methanol

Sources & evidence

ORD record
ord-0591013fd92545f5bf5092992c26919f
Source dataset
uspto-grants-1998_03
Patent number
US05726197

Linked notes

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