Hydrochloric Acid → HCID 14674417, compound

HRID 2249305Notes

Reaction equation

HRID 2249305 reaction equation
[CH3:1][N:2]([CH3:14])[C:3](=[S:13])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1.C([Mg]Br)(C)C.[C:20]1(=[O:26])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1.Cl>C1(C)C=CC=CC=1.C(OC)(C)(C)C>[CH3:14][N:2]([CH3:1])[C:3](=[S:13])[CH:4]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1)[C:20]1([OH:26])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7967CyclohexanoneHCID 156403Benzeneethanethioamide, 4-methoxy-N,N-dimethyl-HCID 178418365HCID 178418365, compound

Product 1

HCID 14674417HCID 14674417, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent3×HCID 15413tert-Butyl methyl etherSolvent

Procedure

N,N-Dimethyl-p-methoxyphenylthioacetamide (20.9 g) in toluene was added to a solution of 1.45M isopropyl magnesium bromide in methyl t-butyl ether (80 ml) and toluene (400 ml) under an inert atmosphere of nitrogen whilst the internal temperature was maintained below 10° C. After 2 hours a solution of cyclohexanone (9.82 g) in toluene (50 ml) was added to the reaction mixture under nitrogen. After a further 15 minutes the mixture was blown over onto 1N hydrochloric acid (150 ml). The organic phase was washed, dried and evaporated. Recrystallisation of the residue from di-isopropyl ether gave the title compound (19.3 g, 64% yield), melting point 132° to 3° C.

Workup

  1. temperaturewas maintained below 10° C
  2. washThe organic phase was washed
  3. customdried
  4. customevaporated
  5. customRecrystallisation of the residue from di-isopropyl ether

Sources & evidence

ORD record
ord-ee6a880b274444b6aa7077881dbb73b2
Source dataset
uspto-grants-1991_08
Patent number
US05043466

Reaction notes

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