Hydrochloric Acid → HCID 18960736, compound

HRID 1463313Notes

Reaction equation

HRID 1463313 reaction equation
Cl.[N+:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[S:11][C:12]1[N:13]([C:17]2[CH:41]=[CH:40][C:20]([C:21]([N:23]3[CH2:28][CH2:27][CH:26]([N:29]4[C:39]5[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=5)[CH2:33][CH2:32][C:30]4=[O:31])[CH2:25][CH2:24]3)=[O:22])=[CH:19][CH:18]=2)[CH:14]=[CH:15][N:16]=1)([O-])=O.O.[OH-].[Na+]>C(O)C>[NH2:2][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[S:11][C:12]1[N:13]([C:17]2[CH:41]=[CH:40][C:20]([C:21]([N:23]3[CH2:28][CH2:27][CH:26]([N:29]4[C:39]5[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=5)[CH2:33][CH2:32][C:30]4=[O:31])[CH2:25][CH2:24]3)=[O:22])=[CH:19][CH:18]=2)[CH:14]=[CH:15][N:16]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 18960753HCID 18960753, compound

Product 1

HCID 18960736HCID 18960736, compoundYield 84.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To the mixture of conc. hydrochloric acid (3.2 ml) and ethanol (2 ml) is added 1-[1-{4-[2-(2-nitrophenyl)thio-1-imidazolyl]benzoyl}-4-piperidinyl]-3,4-dihydrocarbostyril (2.0 g), and thereto is added dropwise a solution of stannous chloride dihydrate (2.7 g) in ethanol (4 ml) at a temperature below 25° C. with water-cooling, and the mixture is stirred at room temperature for two hours. The mixture is poured into ice-water and basified with aqueous sodium hydroxide solution, extracted with chloroform, washed with water, and dried over sodium sulfate. After concentrated under reduced pressure, the resulting residue is purified by silica gel column chromatography (eluent; chloroform: methanol=50:1-25:1), and further dissolved in methanol. The mixture is added dropwise with stirring into water (about 40 ml) and the resulting precipitates are collected by filtration and dried to give 1-[1-{4-[2-(2-aminophenyl)thio-1-imidazolyl]benzoyl}-4-piperidinyl}-3,4-dihydrocarbostyril (1.6 g) as white powder.

Workup

  1. temperaturecooling
  2. extractionextracted with chloroform
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationAfter concentrated under reduced pressure
  6. customthe resulting residue is purified by silica gel column chromatography (eluent; chloroform: methanol=50:1-25:1)
  7. dissolutionfurther dissolved in methanol
  8. additionThe mixture is added dropwise
  9. stirringwith stirring into water (about 40 ml)
  10. customthe resulting precipitates
  11. filtrationare collected by filtration
  12. customdried

Sources & evidence

ORD record
ord-c1f9dd0c5a884f23bd92e702a4908145
Source dataset
uspto-grants-1994_04
Patent number
US05300513

Reaction notes

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