Hydrochloric Acid → HCID 19090443, compound

HRID 892626Notes

Reaction equation

HRID 892626 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:10]2[S:11][C:12]3[NH:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]=3[N:19]=2)[CH:6]=[CH:7][C:8]=1[CH3:9])#[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:4]=[C:5]([C:10]2[S:11][C:12]3[NH:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]=3[N:19]=2)[CH:6]=[CH:7][C:8]=1[CH3:9]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 19090459HCID 19090459, compound

Product 1

HCID 19090443HCID 19090443, compoundYield 22.7%

Reagents, catalysts & solvents 3

HCID 517166Dichlorocobalt hexahydrateCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Then, a solution of 2-(3-cyano-4-methylphenyl)-5,6,7,8-tetrahydro-4H-thiazolo[5,4-b]azepine (6.12 g) and cobalt chloride hexahydrate (10.8 g) in a mixture of methanol (30 ml) and tetrahydrofuran (20 ml) was ice-cooled, followed by adding a powder of sodium borohydride (8.6 g) gradually, and further stirred for 1 hr. at the same 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 to remove the solvent. The residue was purified by a column chromatography on silica gel, and neutralized with hydrogen chloride to give the title compound (yield 22.7%). m.p. 245°-248° (recrystallized from methanol).

Workup

  1. temperaturecooled
  2. extractionthe reaction mixture was extracted with diethyl ether
  3. extractionextracted with chloroform
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. distillationdistilled under reduced pressure
  6. customto remove the solvent
  7. customThe residue was purified by a column chromatography on silica gel

Sources & evidence

ORD record
ord-316c39e7f5374ac796d093c48fdd1afa
Source dataset
uspto-grants-1992_06
Patent number
US05118806

Reaction notes

Loading…