Water → HCID 67594897, compound

HRID 613507Notes

Reaction equation

HRID 613507 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([NH:12][C:13](=[O:22])[C:14]3[C:19]([Cl:20])=[CH:18][CH:17]=[CH:16][C:15]=3[Cl:21])[CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[C:23](OCC)=[O:24].[SH:28][C:29]1[NH:30][CH:31]=[CH:32][N:33]=1.O>CN1CCCC1=O>[Cl:21][C:15]1[CH:16]=[CH:17][CH:18]=[C:19]([Cl:20])[C:14]=1[C:13]([NH:12][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:6]=1[N:5]=[CH:4][C:3]1[C:23](=[O:24])[N:30]3[CH:31]=[CH:32][N:33]=[C:29]3[S:28][C:2]2=1)=[O:22]

Participants

5

Reactant 3

HCID 962WaterHCID 19592702HCID 19592702, compoundHCID 178527877HCID 178527877, compound

Product 1

HCID 67594897HCID 67594897, compoundYield 94.9%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 4-chloro-8-(2,6-dichlorobenzoylamino)-3-ethoxycarbonylquinoline (251 mg) in N-methylpyrrolidone (2 ml) was added 2-mercaptoimidazole (89 mg), and the mixture was stirred for 1 hour at 65° C. The mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with saturated ammonium chloride solution, saturated sodium bicarbonate solution and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was crystallized from ethanol to give 4-(2,6-dichlorobenzoylamino)-7H-imidazo[2',1':2,3][1,3]thiazino-[5,6-c]quinolin-7-one (248.2 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated ammonium chloride solution, saturated sodium bicarbonate solution and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was crystallized from ethanol

Sources & evidence

ORD record
ord-aa5dc3e3353044408bb00f2862927126
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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