Hydrochloric Acid → HCID 9885335, compound

HRID 581091Notes

Reaction equation

HRID 581091 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([C:9]([OH:11])=O)[S:7][CH:8]=1)(=[O:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.[Cl:24][C:25]1[CH:26]=[C:27]2[C:31](=[CH:32][CH:33]=1)[N:30]([C:34]([NH2:36])=[O:35])[C:29](=[O:37])[CH2:28]2.Cl>CN(C)C=O.CN(C1C=CN=CC=1)C>[Cl:24][C:25]1[CH:26]=[C:27]2[C:31](=[CH:32][CH:33]=1)[N:30]([C:34]([NH2:36])=[O:35])[C:29](=[O:37])[CH:28]2[C:9](=[O:11])[C:6]1[S:7][CH:8]=[C:4]([C:1](=[O:3])[CH3:2])[CH:5]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 682631,1'-CarbonyldiimidazoleHCID 98591595-Chloro-2-oxo-2,3-dihydro-1H-indole-1-carboxamideHCID 131564014-Acetylthiophene-2-carboxylic acid

Product 1

HCID 9885335HCID 9885335, compoundYield 22%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent2×

Procedure

A 0.78 g (4.59 nmuoles) sample of 4-acetyl-2-thio-phenecarboxylic acid (prepared according to Satonaka, H., Bull. Chem. Soc. Japan 56:2463 (1983)) was combined with 0.95 g (5.85 mmoles) of 1,1'-carbonyldiimidazole in 10 ml of N,N-dimethylformamide and stirred at room temperature under argon atmosphere. After two hours the reaction contents were transferred to an addition funnel and slowly added to a slurry of 0.88 g (4.18 mmoles) of 5-chloro-2-oxindole-1-carboxamide and 1.38 g (11.28 mmoles) of 4-(N,N-dimethylamino)pyridine in 30 ml of N,N-dimethylformamide stirring at 5° C. (ice bath) under an inert atmosphere. The reaction contents were stirred for fifteen minutes at 5° C. after complete addition followed by twenty-four hours at room temperature. Pouring the reaction mixture into 110 ml of 0.3N hydrochloric acid cause the precipitation of a greenish-yellow solid. Filtration followed by sequential washing with 3N hydrochloric acid and water, provided the crude product which was recrystallized twice from acetic acid to give 0.34 g (0.94 mmoles, 22% yield) of pure 5-chloro-3-(4-acetyl-2-thenoyl)-2-oxindole-1-carboxamide as a greenish-yellow solvated complex with 0.2 equivalents of acetic acid, m.p. 230-233° C.

Workup

  1. customAfter two hours the reaction contents
  2. customwere transferred to an addition funnel
  3. customThe reaction contents
  4. stirringwere stirred for fifteen minutes at 5° C.
  5. additionafter complete addition
  6. waitfollowed by twenty-four hours at room temperature
  7. customthe precipitation of a greenish-yellow solid
  8. filtrationFiltration
  9. washby sequential washing with 3N hydrochloric acid and water
  10. customprovided the crude product which
  11. customwas recrystallized twice from acetic acid

Sources & evidence

ORD record
ord-11d033a1dd54416785647c3a19a8fd20
Source dataset
uspto-grants-1999_07
Patent number
US05919809

Reaction notes

Loading…