Hydrochloric Acid → HCID 19090376, compound

HRID 1463478Notes

Reaction equation

HRID 1463478 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:10][C:11]3[NH:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]=3[N:18]=2)=[CH:5][C:4]=1[CH3:19])#[N:2].[BH4-].[Na+].[ClH:22]>CO.O1CCCC1.O.O.O.O.O.O.[Co](Cl)Cl>[ClH:22].[ClH:22].[NH2:2][CH2:1][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:10][C:11]3[NH:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]=3[N:18]=2)=[CH:5][C:4]=1[CH3:19]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 15069584HCID 15069584, compound

Product 1

HCID 19090376HCID 19090376, compoundYield 20.1%

Reagents, catalysts & solvents 3

HCID 517166Dichlorocobalt hexahydrateCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(4-cyano-3-methylphenyl)-5,6,7,8-tetrahydro-4H-thiazolo[5,4-b]azepine (20 g) and cobalt chloride hexahydrate (35.3 g) in a mixture of methanol (90 ml) and tetrahydrofuran (60 ml) was ice-cooled, followed by addition of a powder of sodium borohydride (33.1 g) gradually, and further stirred for 20 hrs. at room temperature. After acidifying with an aqueous 4N-hydrochloric acid, the reaction mixture was extracted with diethyl ether. The aqueous layer was alkalified with an aqueous ammonia and extracted with chloroform. The extract was dried over anhydrous magnesium sulfate, and distilled under reduced pressure The residue was purified by a column chromatogarphy on silica gel, and neutralized with hydrogen chloride to give the title compound (yield 20.1%).

Workup

  1. temperaturecooled
  2. customat room temperature
  3. extractionthe reaction mixture was extracted with diethyl ether
  4. extractionextracted with chloroform
  5. dry with materialThe extract was dried over anhydrous magnesium sulfate
  6. distillationdistilled under reduced pressure The residue
  7. customwas purified by a column chromatogarphy on silica gel

Sources & evidence

ORD record
ord-fb93d5344fc4413d91aeb6259187bba4
Source dataset
uspto-grants-1994_04
Patent number
US05300639

Reaction notes

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