5-Chloro-2-oxo-2,3-dihydro-1H-indole-1-carboxamide → HCID 70221831, compound

HRID 728369Notes

Reaction equation

HRID 728369 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([C:10](Cl)=[O:11])[S:8][CH:9]=1)(=[O:4])=[O:3].[Cl:13][C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[N:19]([C:23]([NH2:25])=[O:24])[C:18](=[O:26])[CH2:17]2>CN(C1C=CN=CC=1)C.C(O)(=O)C>[Cl:13][C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[N:19]([C:23]([NH2:25])=[O:24])[C:18](=[O:26])[CH:17]2[C:10](=[O:11])[C:7]1[S:8][CH:9]=[C:5]([S:2]([CH3:1])(=[O:4])=[O:3])[CH:6]=1

Participants

5

Reactant 2

HCID 98591595-Chloro-2-oxo-2,3-dihydro-1H-indole-1-carboxamideHCID 21266037HCID 21266037, compound

Product 1

HCID 70221831HCID 70221831, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 176Acetic AcidSolvent

Procedure

The title compound was prepared according to the procedure of Example 32. The reaction of 10 ml of thionyl chloride with 1.39 g (6.7 mmoles) of 4-methylsulfonyl-2-thiophenecarboxylic acid (prepared according to Arndt, F., et al., Chem. Ber. 94:1757 (1961)) gave 1.54 g of the crude acid chloride as a solid. The entire amount of 4-methylsulfonyl-2-thiophenecarbonyl chloride was coupled to 1.28 g (6.1 mmoles) of 5-chloro-2-oxindole-1-carboxamide in the presence of 2.24 g (18.3 mmoles) 4-(N,N-dimethylamino)pyridine. Acidic workup gave 2.28 g of crude product as an orange solid. Recrystallization from -butanone gave two crops of slightly impure yellow crystalline solid which had a combined mass of 2.18 g. Further purification by recrystallization provided 1.19 g (2.98 mmoles, 49% yield) of pure 5-chloro-3-(4-methylsulfonyl-2-thenoyl)-2-oxindole-1-carboxamide as a yellow crystalline solid, m.p. 228°-30° C. (acetic acid).

Workup

  1. customAcidic workup gave 2.28 g of crude product as an orange solid
  2. customRecrystallization from -butanone
  3. customgave two crops of slightly impure yellow crystalline solid which
  4. customFurther purification
  5. customby recrystallization

Sources & evidence

ORD record
ord-2ca358ef8c0e402f80fa973ab6ba159d
Source dataset
uspto-grants-1991_09
Patent number
US05047554

Reaction notes

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