Hydrochloric Acid → HCID 13565557, compound

HRID 1589380Notes

Reaction equation

HRID 1589380 reaction equation
[C:1]([NH:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([Cl:17])[CH:15]=2)[CH2:10][C:9]1=[O:18])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:19]1([C:24](Cl)=[O:25])[S:23][CH:22]=[CH:21][CH:20]=1.O.Cl>CN(C1C=CN=CC=1)C.CN(C)C=O>[C:1]([NH:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([Cl:17])[CH:15]=2)[CH:10]([C:24](=[O:25])[C:19]2[S:23][CH:22]=[CH:21][CH:20]=2)[C:9]1=[O:18])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 789282-Thiophenecarbonyl chlorideHCID 13565641HCID 13565641, compound

Product 1

HCID 13565557HCID 13565557, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent2×

Procedure

A solution of 667 mg (2.5 mmole) of N-t-butyl-6-chloro-2-oxindole-1-carboxamide and 684 mg (5.6 mmole) of 4-(N,N-dimethylamino)pyridine in 8 ml of N,N-dimethylformamide was cooled in an ice-bath, and then a solution of 410 mg (2.8 mmole) of 2-thenoyl chloride in 2 ml of N,N-dimethylformamide was added dropwise, with stirring. Stirring was continued for ca. 30 minutes, and then the reaction mixture was poured into a mixture of 60 ml of water and 2.5 ml of 3N hydrochloric acid. The resulting mixture was cooled in an ice-bath, and then the solid was recovered by filtration and recrystallized from ca. 30 ml of acetic acid. This afforded 425 mg of the title compound as yellow crystals, mp 160.5°-161.5° C. (slight decomposition).

Workup

  1. stirringStirring
  2. temperatureThe resulting mixture was cooled in an ice-bath
  3. filtrationthe solid was recovered by filtration
  4. customrecrystallized from ca. 30 ml of acetic acid

Sources & evidence

ORD record
ord-5e2adfd191a34fafb97874a1b4de047a
Source dataset
uspto-grants-1986_02
Patent number
US04569942

Reaction notes

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