Carbon Dioxide → HCID 178490626, compound

HRID 616941Notes

Reaction equation

HRID 616941 reaction equation
C1(C)C=CC(S([NH:10][N:11]=[C:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[NH:14][C:13]2=[O:21])(=O)=O)=CC=1.C(Cl)[Cl:24].[C:26](=[O:28])=O>[OH-].[Na+]>[Cl:24][C:19]1[CH:18]=[CH:17][C:16]([O:28][CH3:26])=[C:15]2[C:20]=1[C:12](=[N+:11]=[N-:10])[C:13](=[O:21])[NH:14]2

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 6344Dichloromethane2×HCID 178427623HCID 178427623, compound

Product 1

HCID 178490626HCID 178490626, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

30.0 g (0.079 mole) of the isatin-3-p-toluenesulfonylhydrazone (prepared in part A) is suspended in 900 ml 0.2 N NaOH and heated slightly for ~30 minutes. The mixture is stirred for 22 hours at room temperature with a layer of methylene chloride (300 ml). The methylene chloride is stripped off and the aqueous phase saturated with CO2 (dry ice used). The light peach-colored precipitates are filtered off, washed with a small amount of H2O and dried in vacuo at 45° for 11/2 hours to give 19.2 g of title compound (Theor. yield = 17.7 g). The crude product is taken up in 1.8 1. CH3OH and the clear light red solution concentrated down to a volume of 500 ml, cooled, filtered and dried overnight in vacuo at room temperature. Yield of title compound is 15.2 g, m.p. 206°-207°, light orange crystals.

Workup

  1. temperatureheated slightly for ~30 minutes
  2. customThe light peach-colored precipitates
  3. filtrationare filtered off
  4. washwashed with a small amount of H2O
  5. customdried in vacuo at 45° for 11/2 hours

Sources & evidence

ORD record
ord-a0fa42ccc1f14d31a63e9e9ca6ea90c9
Source dataset
uspto-grants-1978_02
Patent number
US04076818

Reaction notes

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