Hydrochloric Acid → HCID 53654790, compound

HRID 1701156Notes

Reaction equation

HRID 1701156 reaction equation
[CH3:1][O:2][C:3](=[O:6])[CH2:4][SH:5].[K].Cl[CH:9]([C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[F:24])=[CH:14][CH:13]=1)[CH2:10][CH3:11].FC1C=CC=CC=1C1C=CC(CCC(CCC2C=CC(C3C=CC=CC=3F)=CC=2)=O)=CC=1.[BH4-].[Na+].OC(C1C=CC(C2C=CC=CC=2F)=CC=1)CC.Cl>CN(C)C=O.C1C=CC=CC=1.C(OCC)(=O)C.O>[CH3:1][O:2][C:3](=[O:6])[CH2:4][S:5][CH:9]([C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[F:24])=[CH:14][CH:13]=1)[CH2:10][CH3:11]

Participants

12

Reactant 7

HCID 313Hydrochloric AcidHCID 16907Methyl ThioglycolateHCID 27411701-[4-(2-fluorophenyl)phenyl]propan-1-olHCID 27816854-(1-chloropropyl)-2'-fluoro-1,1'-biphenylHCID 4311764Sodium borohydrideHCID 5462222PotassiumHCID 53921419HCID 53921419, compound

Product 1

HCID 53654790HCID 53654790, compound

Reagents, catalysts & solvents 4

HCID 241BenzeneSolventHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

101.5 gm (0.905 mol) of potassium tert. butylate, suspended in 500 ml of dimethylformamide, were admixed, while stirring and cooling under exclusion of air, with 96.0 gm (0.905 mol) of thioglycolic acid methyl ester. To the solution of the potassium salt, the mixture was admixed with 205.9 gm (0.822 mol) of 1-chloro-1-(2'-fluoro-4-biphenylyl)propane [prepared by reduction of 2'-fluoro-4-biphenylylethylketone with sodium borohydride and subsequent reaction of the obtained 1-hydroxy-1-(2'-fluoro-4-biphenylyl)-propane with hydrochloric acid in benzene], and the mixture was stirred for 4 hours at room temperature. Subsequently, 2 liters of water were added, and the reaction product was isolated by extraction with ethyl acetate, and washing, drying and evaporating of the extract. Yield: 254 gm (97% of theory); oil, Rf -value: 0.5 (cyclohexane-ethyl acetate=9:1 on silicagel-polygram-plates).

Workup

  1. stirringwas stirred for 4 hours at room temperature
  2. washwashing
  3. customdrying
  4. customevaporating of the extract

Sources & evidence

ORD record
ord-01ce837632ba4e898c2668b0e326a1f6
Source dataset
uspto-grants-1980_03
Patent number
US04191776

Reaction notes

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