Cyclohexyl isothiocyanate → 5-(3-bromophenyl)-N-cyclohexyl-6,6-dimethyl-4,4-dioxo-5H-1,4,3-oxathiazin-2-amine

HRID 339837Notes

Reaction equation

HRID 339837 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]([S:13]([NH2:16])(=[O:15])=[O:14])[C:9]([OH:12])([CH3:11])[CH3:10])[CH:5]=[CH:6][CH:7]=1.[CH:17]1([N:23]=[C:24]=S)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].BrN1C(=O)CCC1=O>CN1C(=O)CCC1.O>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]2[C:9]([CH3:10])([CH3:11])[O:12][C:24]([NH:23][CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)=[N:16][S:13]2(=[O:14])=[O:15])[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 14289Cyclohexyl isothiocyanateHCID 67184N-bromobutanimideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 682918601-(3-Bromophenyl)-2-hydroxy-2-methylpropane-1-sulfonamide

Product 1

HCID 1784316525-(3-bromophenyl)-N-cyclohexyl-6,6-dimethyl-4,4-dioxo-5H-1,4,3-oxathiazin-2-amineYield 30.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 1.00 g of 1-(3-bromophenyl)-2-hydroxy-2-methylpropane-1-sulfonamide and 0.483 g of cyclohexyl isothiocyanate in 7 ml of NMP was admixed with 1.62 ml of a 2 N solution of sodium bis(trimethylsilyl)amide. After stirring for 20 minutes, 578 mg of N-bromosuccinimide were added and the mixture was stirred at room temperature for a further 60 minutes. The reaction solution was admixed with 150 ml of water and extracted twice with 150 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 lyophilized. This gave the product (411 mg) with a molecular weight of 415.3 g/mol (C17H23BrN2O3S); MS (ESI): m/e=416 (M+H+).

Workup

  1. stirringthe mixture was stirred at room temperature for a further 60 minutes
  2. extractionextracted twice with 150 ml of ethyl acetate
  3. washThe combined organic phases were washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated by rotary evaporation
  6. customThe residue was purified in a purification laboratory by means of preparative HPLC

Sources & evidence

ORD record
ord-8ce43c30f4304a5ead42fccd4491284e
Source dataset
uspto-grants-2014_11
Patent number
US08895547B2

Reaction notes

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