1-(2-Ethylbutyl)cyclohexanecarbonyl chloride → HCID 86642989, compound

HRID 1925182Notes

Reaction equation

HRID 1925182 reaction equation
[NH2:1][C:2]1[C:3]([SH:12])=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[CH2:13]([CH:15]([CH2:26][CH3:27])[CH2:16][C:17]1([C:23](Cl)=[O:24])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)[CH3:14]>N1C=CC=CC=1>[CH2:13]([CH:15]([CH2:26][CH3:27])[CH2:16][C:17]1([C:23]([NH:1][C:2]2[C:3]([S:12][C:23]([C:17]3([CH2:16][CH:15]([CH2:26][CH3:27])[CH2:13][CH3:14])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]3)=[O:24])=[CH:4][C:5]3[C:10]([CH:11]=2)=[CH:9][CH:8]=[CH:7][CH:6]=3)=[O:24])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)[CH3:14]

Participants

4

Reactant 2

HCID 106571251-(2-Ethylbutyl)cyclohexanecarbonyl chlorideHCID 132351653-Amino-2-naphthalenethiol

Product 1

HCID 86642989HCID 86642989, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 3-amino-naphthalene-2-thiol in pyridine are added two mol equivalents of 1-(2-ethyl-butyl)-cyclohexanecarbonyl chloride at room temperature. After completion of the addition, the reaction mixture is heated to 60° C. for 2 hours. The pyridine is then removed under reduced pressure, water is added and the mixture is extracted with ethyl acetate. The combined extracts are washed with sat. NaHCO3-solution, diluted hydrochloric acid and brine, dried (Na2SO4) and concentrated to obtain crude 1-(2-ethyl-butyl)-cyclohexanecarbothioic acid S-(3-{[1-(2-ethyl-butyl)-cyclohexanecarbonyl]-amino}-naphthalen-2-yl)ester.

Workup

  1. additionAfter completion of the addition
  2. customThe pyridine is then removed under reduced pressure, water
  3. additionis added
  4. extractionthe mixture is extracted with ethyl acetate
  5. washThe combined extracts are washed with sat. NaHCO3-solution, diluted hydrochloric acid and brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-76691cd0dce34af4b45e9e1322a44b58
Source dataset
uspto-grants-2012_05
Patent number
US08178583B2

Reaction notes

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