Cyclohexyl isothiocyanate → HCID 178431656, compound

HRID 339856Notes

Reaction equation

HRID 339856 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]([S:20]([NH2:23])(=[O:22])=[O:21])[C:16]([OH:19])([CH3:18])[CH3:17])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:24]1([N:30]=[C:31]=S)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].BrN1C(=O)CCC1=O>CN1C(=O)CCC1.C1COCC1.O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]2[C:16]([CH3:18])([CH3:17])[O:19][C:31]([NH:30][CH:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)=[N:23][S:20]2(=[O:22])=[O:21])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 14289Cyclohexyl isothiocyanate2×HCID 67184N-bromobutanimideHCID 2724254Sodium bis(trimethylsilyl)amide2×HCID 68291290HCID 68291290, compound

Product 1

HCID 178431656HCID 178431656, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

At room temperature, a solution of 1.00 g of 1-(3-benzyloxyphenyl)-2-hydroxy-2-methylpropane-1-sulfonamide and 0.45 ml of cyclohexyl isothiocyanate in 6.5 ml of NMP was admixed with 1.49 ml of a 2 N solution of sodium bis(trimethylsilyl)amide in THF. After stirring for 45 minutes, the conversion was checked by means of LCMS. Since the reaction was still incomplete, an additional 0.22 ml cyclohexyl isothiocyanate and 0.74 ml of a 2 N solution of sodium bis(trimethylsilyl)amide in THF were added. After stirring for 20 minutes, 0.53 g of N-bromosuccinimide was added and the mixture was stirred at room temperature for a further hour. The reaction solution was admixed with 150 ml of water and extracted twice with 100 ml of ethyl acetate. The combined organic phases were washed with saturated aqueous sodium chloride solution, dried over MgSO4 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 lyophilized. This gave the product (587 mg) with a molecular weight of 442.6 g/mol (C24H30N2O4S); MS (ESI): m/e=443 (M+H+).

Workup

  1. customAt room temperature
  2. stirringAfter stirring for 20 minutes
  3. stirringthe mixture was stirred at room temperature for a further hour
  4. extractionextracted twice with 100 ml of ethyl acetate
  5. washThe combined organic phases were washed with saturated aqueous sodium chloride solution
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated by rotary evaporation
  8. customThe residue was purified in a purification laboratory by means of preparative HPLC

Sources & evidence

ORD record
ord-811efb84a3524f8cba70f0b2137a1690
Source dataset
uspto-grants-2014_11
Patent number
US08895547B2

Reaction notes

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