Hydrochloric Acid → 5-(4,5,7-Trifluorobenzothiazol-2-ylthio)pentanoic acid ethyl ester

HRID 1940628Notes

Reaction equation

HRID 1940628 reaction equation
[H-].[Na+].[F:3][C:4]1[C:9]2[N:10]=[C:11]([SH:13])[S:12][C:8]=2[C:7]([F:14])=[CH:6][C:5]=1[F:15].Br[CH2:17][CH2:18][CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22].Cl>CN(C=O)C.O>[CH2:24]([O:23][C:21](=[O:22])[CH2:20][CH2:19][CH2:18][CH2:17][S:13][C:11]1[S:12][C:8]2[C:7]([F:14])=[CH:6][C:5]([F:15])=[C:4]([F:3])[C:9]=2[N:10]=1)[CH3:25]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 84580Ethyl 5-bromovalerateHCID 178505914HCID 178505914, compound

Product 1

HCID 538517315-(4,5,7-Trifluorobenzothiazol-2-ylthio)pentanoic acid ethyl esterYield 64%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent3×

Procedure

Sodium hydride (60% in oil, 220 mg, 5.5 mmol) was suspended in DMF (2 ml) and the suspension was stirred on a water bath. To the suspension was added dropwise a solution of 4,5,7-trifluoro-2-mercaptobenzothiazole (1.1 g, 5 mmol) in DMF (5 ml) under ice cooling and the mixture was stirred for 30 min. at room temperature and then cooled on a water bath. To the cooled mixture was added dropwise a solution of ethyl 5-bromopentanoate (1.05 g, 5 mmol) in DMF (3 ml) and the mixture was stirred for 2 hours at room temperature. The resultant mixture was diluted with water, then acidified with 7% hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with an aqueous saturated saline solution, dried and then evaporated. The resulting residue was purified on a silica gel column to give 5-(4,5,7-trifluorobenzothiazol-2-ylthio)pentanoic acid ethyl ester (1.1 g, 64%) as an oil.

Workup

  1. stirringthe mixture was stirred for 30 min. at room temperature
  2. temperaturecooled on a water bath
  3. stirringthe mixture was stirred for 2 hours at room temperature
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with an aqueous saturated saline solution
  6. customdried
  7. customevaporated
  8. customThe resulting residue was purified on a silica gel column

Sources & evidence

ORD record
ord-e4104a4d4dae4aa6a0318ba7d49a8309
Source dataset
uspto-grants-1997_12
Patent number
US05700819

Reaction notes

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