Cyclohexyl isothiocyanate → HCID 178431653, compound

HRID 339822Notes

Reaction equation

HRID 339822 reaction equation
[OH:1][C:2]([CH3:15])([CH3:14])[CH:3]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[S:4]([NH2:7])(=[O:6])=[O:5].[CH:16]1([N:22]=[C:23]=S)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].BrN1C(=O)CCC1=O>CN1C(=O)CCC1.C1COCC1.O>[CH:16]1([NH:22][C:23]2[O:1][C:2]([CH3:15])([CH3:14])[CH:3]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[S:4](=[O:5])(=[O:6])[N:7]=2)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

8

Reactant 4

HCID 14289Cyclohexyl isothiocyanateHCID 67184N-bromobutanimideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 68291332HCID 68291332, compound

Product 1

HCID 178431653HCID 178431653, compoundYield 20.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 150 mg of 2-hydroxy-2-methyl-1-phenylpropane-1-sulfonamide and 97 mg of cyclohexyl isothiocyanate in 1.5 ml of NMP was admixed with 0.20 ml of a 2 N solution of sodium bis(trimethylsilyl)amide in THF. After stirring for 20 minutes, 71 mg of N-bromosuccinimide were added and the mixture was stirred at room temperature for a further 15 minutes. The reaction solution was admixed with 50 ml of water and extracted twice with 50 ml of ethyl acetate. The combined organic phases were dried over Na2SO4 and concentrated by rotary evaporation. The residue was purified in a purification laboratory by means of preparative HPLC, and the product-containing fractions were freed of the organic solvent under reduced pressure. The aqueous residue was extracted three times with dichloromethane, and the combined organic phases were dried using a phase separator cartridge (Chromabond® PTS) and concentrated by rotary evaporation. The residue was dissolved in a mixture of acetonitrile and water and lyophilized. This gave the product (46 mg) with a molecular weight of 336.4 g/mol (C17H24N2O3S); MS (ESI): m/e=337 (M+H+).

Workup

  1. stirringthe mixture was stirred at room temperature for a further 15 minutes
  2. extractionextracted twice with 50 ml of ethyl acetate
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. concentrationconcentrated by rotary evaporation
  5. customThe residue was purified in a purification laboratory by means of preparative HPLC
  6. extractionThe aqueous residue was extracted three times with dichloromethane
  7. customthe combined organic phases were dried
  8. concentrationconcentrated by rotary evaporation
  9. dissolutionThe residue was dissolved in a mixture of acetonitrile and water

Sources & evidence

ORD record
ord-7fdb04cb2c874ac394c2a36184f4743d
Source dataset
uspto-grants-2014_11
Patent number
US08895547B2

Reaction notes

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