Hydrochloric Acid → HCID 178505910, compound

HRID 1735886Notes

Reaction equation

HRID 1735886 reaction equation
[C:1]([C:3]1[N:7]([CH:8]2[CH2:17][CH2:16][C:15]3[C:10](=[CH:11][C:12]([F:19])=[CH:13][C:14]=3[F:18])[CH2:9]2)[C:6](=[S:20])[NH:5][CH:4]=1)#[N:2].C1(C)C=CC=CC=1.Cl.O.[F-].[K+].C([Sn]([N:45]=[N+:46]=[N-:47])(CCCC)CCCC)CCC>C(OCC)C.O.C(OCC)(=O)C>[F:18][C:14]1[CH:13]=[C:12]([F:19])[CH:11]=[C:10]2[C:15]=1[CH2:16][CH2:17][CH:8]([N:7]1[C:3]([C:1]3[NH:47][N:46]=[N:45][N:2]=3)=[CH:4][NH:5][C:6]1=[S:20])[CH2:9]2

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 4984872Tributyltin azideHCID 196993915-Cyano-1-(5,7-difluoro-1,2,3,4-tetrahydronaphthalen-2-yl)-1,3-dihydroimidazole-2-thioneHCID 23675105Potassium fluoride hydrate

Product 1

HCID 178505910HCID 178505910, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5-cyano-1-(5,7-difluoro-1,2,3,4-tetrahydronaphthalen-2-yl)-1,3-dihydroimidazole-2-thione (0,554 g, 1.9 mmol), prepared as in Example 19, in 1.6 mL of tributyltin azide was heated at 130° C. under a nitrogen atmosphere for 2.5 hours and then 10 mL of toluene was added. The mixture was allowed to cool to room temperature and approximately 5 mL of diethyl ether was added. The mixture was cooled to 0° C. and then treated with 10 mL of 1N hydrogen chloride in diethyl ether for approximately 15 minutes. The mixture was poured into a solution of potassium fluoride monohydrate (15.0 g) in 15 to 20 mL of water and 75 mL of ethyl acetate. The ethyl acetate layer was extracted with 2N sodium hydroxide and the aqueous layer was washed 6 times with methylene chloride. The aqueous layer was acidified with concentrated hydrochloric acid and then extracted with ethyl acetate. Evaporation of the solvents gave 1-(5,7-difluoro-1,2,3,4-tetrahydronaphthalen-2-yl)-5(1H)-tetrazol-5-yl-1,3-dihydroimidazole-2-thione (0.57 g, 1.7 mmol), m.p. 214°-215° C.

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. extractionThe ethyl acetate layer was extracted with 2N sodium hydroxide
  3. washthe aqueous layer was washed 6 times with methylene chloride
  4. extractionextracted with ethyl acetate
  5. customEvaporation of the solvents

Sources & evidence

ORD record
ord-ccaf2ad7d4554cf4ad995f061ee395b8
Source dataset
uspto-grants-1996_07
Patent number
US05538988

Reaction notes

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