Cyclohexylamine → HCID 178431657, compound

HRID 72360Notes

Reaction equation

HRID 72360 reaction equation
[CH3:1][C:2]1([CH3:22])[C:7]([CH3:9])([CH3:8])[O:6][C:5](OC2C=CC([N+]([O-])=O)=CC=2)=[N:4][S:3]1(=[O:21])=[O:20].[CH:23]1([NH2:29])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1>ClCCl>[CH:23]1([NH:29][C:5]2[O:6][C:7]([CH3:8])([CH3:9])[C:2]([CH3:1])([CH3:22])[S:3](=[O:20])(=[O:21])[N:4]=2)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

4

Reactant 2

HCID 7965CyclohexylamineHCID 718136815,5,6,6-Tetramethyl-2-(4-nitrophenoxy)-5,6-dihydro-1,4,3-oxathiazine 4,4-dioxide

Product 1

HCID 178431657HCID 178431657, compoundYield 23.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

200 mg of 5,5,6,6-tetramethyl-2-(4-nitrophenoxy)-5,6-dihydro-1,4,3-oxathiazine 4,4-dioxide and 60 mg of cyclohexylamine were dissolved in 2 ml of dichloromethane, and the mixture was stirred at room temperature for 15 minutes. Subsequently, the reaction solution was diluted with 50 ml of dichloromethane, washed twice with 50 ml of 0.1 N aqueous sodium hydroxide solution, twice with 50 ml of 1 N aqueous hydrochloric acid and with 50 ml of saturated aqueous sodium hydrogencarbonate solution, dried over Na2SO4 and concentrated by rotary evaporation. This gave the product (41 mg) with a molecular weight of 288.4 g/mol (C13H24N2O3S); MS (ESI): m/e=289 (M+H+).

Workup

  1. washwashed twice with 50 ml of 0.1 N aqueous sodium hydroxide solution, twice with 50 ml of 1 N aqueous hydrochloric acid and with 50 ml of saturated aqueous sodium hydrogencarbonate solution
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-2e70c4a95d664a42b293d26c238706cd
Source dataset
uspto-grants-2014_09
Patent number
US08828994B2

Reaction notes

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