Toluene → HCID 66958552, compound

HRID 1984396Notes

Reaction equation

HRID 1984396 reaction equation
C1(C)C=CC=CC=1.S(Cl)(Cl)=O.[O:12]=[C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15](=[O:22])[N:14]1[CH2:23][CH2:24][C:25]1[N:29]([CH2:30][CH2:31][CH3:32])[N:28]=[C:27]([C:33](O)=[O:34])[CH:26]=1.[OH-].[NH4+:37]>ClCCl>[O:22]=[C:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:13](=[O:12])[N:14]1[CH2:23][CH2:24][C:25]1[N:29]([CH2:30][CH2:31][CH3:32])[N:28]=[C:27]([C:33]([NH2:37])=[O:34])[CH:26]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 14923Ammonium HydroxideHCID 24386Thionyl ChlorideHCID 66958619HCID 66958619, compound

Product 1

HCID 66958552HCID 66958552, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Toluene (70 mL) and thionyl chloride (70 mL) were added to 5-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]-1-propyl-1H-pyrazole-3-carboxylic acid (28.8 g, 87.8 mmol) and the mixture was heated at reflux for 1 hour, cooled to ambient temperature, and concentrated under reduced pressure to yield a yellow solid. The solid was dissolved in dichloromethane (200 mL). The solution was cooled to 0° C., then concentrated ammonium hydroxide (125 mL) was added in one portion. The resulting mixture was stirred for 1 hour at 0° C. The dichloromethane was removed under reduced pressure. A solid was isolated by filtration, washed with water, and dried to afford 28.70 g of 5-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]-1-propyl-1H-pyrazole-3-carboxamide.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 1 hour
  3. concentrationconcentrated under reduced pressure
  4. customto yield a yellow solid
  5. temperatureThe solution was cooled to 0° C.
  6. customThe dichloromethane was removed under reduced pressure
  7. customA solid was isolated by filtration
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-b13a26ad1cde45108d1ff8c1975a571b
Source dataset
uspto-grants-2009_06
Patent number
US07544697B2

Reaction notes

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