5-Chloro-2-oxo-2,3-dihydro-1H-indole-1-carboxamide → HCID 70221211, compound

HRID 728379Notes

Reaction equation

HRID 728379 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]([NH2:13])=[O:12])[C:6](=[O:14])[CH2:5]2.[CH3:15][S:16][C:17]1[O:21][C:20](C(Cl)=O)=[N:19][N:18]=1>CN(C1C=CN=CC=1)C.CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]([NH2:13])=[O:12])[C:6](=[O:14])[CH:5]2[C:20]1[O:21][C:17]([S:16][CH3:15])=[N:18][N:19]=1

Participants

5

Reactant 2

HCID 98591595-Chloro-2-oxo-2,3-dihydro-1H-indole-1-carboxamideHCID 135447285-(Methylsulfanyl)-1,3,4-oxadiazole-2-carbonyl chloride

Product 1

HCID 70221211HCID 70221211, compoundYield 44.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

Using the procedure of Example 32, a 30 ml N,N-dimethylformamide solution of 958 mg (4.55 mmoles) of 5-chloro-2-oxindole-1-carboxamide and 1.50 g (12.28 mmoles) of 4-(N,N-dimethylamino)pyridine was reacted with 975 mg (5.46 mmoles) of 5-methylthio-1,3,4-oxadiazol-2-carbonyl chloride (U.S. Pat. No. 4,001,238). After acidic workup a crude orange solid (1.25 g, 78% Z0 yield) was obtained. Suspension in hot glacial acetic acid followed by filtration furnished the pure title compound (710 mg, 2.01 mmole, 44%) as a bright yellow solid, m.p. 297°-9° C.

Workup

  1. customAfter acidic workup a crude orange solid (1.25 g, 78% Z0 yield)
  2. customwas obtained
  3. filtrationSuspension in hot glacial acetic acid followed by filtration

Sources & evidence

ORD record
ord-c80d8177dac34e5e81494458ea46a51f
Source dataset
uspto-grants-1991_09
Patent number
US05047554

Reaction notes

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