Hydrochloric Acid → HCID 178469664, compound

HRID 613513Notes

Reaction equation

HRID 613513 reaction equation
O.O.O.O.O.O.O.O.O.[S-2:10].[Na+].[Na+].Cl[C:14]1[C:23]2[C:18](=[C:19]([NH:24][C:25](=[O:34])[C:26]3[C:31]([Cl:32])=[CH:30][CH:29]=[CH:28][C:27]=3[Cl:33])[CH:20]=[CH:21][CH:22]=2)[N:17]=[CH:16][C:15]=1[C:35]([O:37][CH2:38][CH3:39])=[O:36].Cl>CN(C)C=O>[Cl:33][C:27]1[CH:28]=[CH:29][CH:30]=[C:31]([Cl:32])[C:26]=1[C:25]([NH:24][C:19]1[CH:20]=[CH:21][CH:22]=[C:23]2[C:18]=1[N:17]=[CH:16][C:15]([C:35]([O:37][CH2:38][CH3:39])=[O:36])=[C:14]2[SH:10])=[O:34]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 73972Sodium sulfide nonahydrateHCID 19592702HCID 19592702, compound

Product 1

HCID 178469664HCID 178469664, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of sodium sulfide nonahydrate (202 mg) in dimethylformamide (5 ml) was dropwise added 4-chloro-8-(2,6-dichlorobenzoylamino)-3-ethoxycarbonylquinoline (297 mg), and the mixture was stirred for 1 hour at ambient temperature. To the mixture was added ice-water, and the mixture was adjusted to pH 3 with 1N hydrochloric acid. The resulting precipitate was collected by filtration and washed with water to give 8-(2,6-dichlorobenzoylamino)-3-ethoxycarbonyl-4-mercaptoquinoline (260 mg).

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. washwashed with water

Sources & evidence

ORD record
ord-32b6fd940d5447d2b52eb0902ec234b7
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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