Succinic anhydride → HCID 19808343, compound

HRID 373855Notes

Reaction equation

HRID 373855 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[S:14][CH2:13][C:12]3[C:11]([C:15](=[O:28])[CH:16]([C:26]#[N:27])[C:17]([NH:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[O:18])=[N:10][N:9]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[C:8]=3[C:6]=2[CH:7]=1.[C:35]1(=[O:41])[O:40][C:38](=[O:39])[CH2:37][CH2:36]1>O1CCCC1>[C:38]([CH2:37][CH2:36][C:35]([NH:1][C:2]1[CH:3]=[CH:4][C:5]2[S:14][CH2:13][C:12]3[C:11]([C:15](=[O:28])[CH:16]([C:26]#[N:27])[C:17]([NH:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[O:18])=[N:10][N:9]([C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=4)[C:8]=3[C:6]=2[CH:7]=1)=[O:41])([OH:40])=[O:39]

Participants

4

Reactant 2

HCID 7922Succinic anhydrideHCID 18962912HCID 18962912, compound

Product 1

HCID 19808343HCID 19808343, compoundYield 67.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-(8-amino-1,4-dihydro-1-phenyl-[1]-benzothiopyrano[4,3-c]pyrazol-3-yl)-2-cyano-3-oxo-N-phenyl-propanamide (1.1 g) dissolved in anhydrous tetrahydrofuran (23 ml) is reacted with succinic anhydride (0.71 g) at the reflux temperature under stirring for 3 hours. After cooling the reaction mixture is diluted with ice water. The precipitate is filtered and washed with water. Crystallization from CHCl3 /methanol yields 0.9 g of 3-[8-(3-carboxy-propanoylamino)-1,4-dihydro-1-phenyl-[1]-benzothiopyrano[4,3-c]pyrazol-3-yl]-2-cyano-3-oxo-N-phenylpropanamide, m.p. 230°-233° C.

Workup

  1. temperatureAfter cooling the reaction mixture
  2. filtrationThe precipitate is filtered
  3. washwashed with water
  4. customCrystallization from CHCl3 /methanol

Sources & evidence

ORD record
ord-ab781dad1638467d93b782f8adc604b4
Source dataset
uspto-grants-1992_11
Patent number
US05166152

Reaction notes

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