Ethylamine → HCID 21910639, compound

HRID 1245286Notes

Reaction equation

HRID 1245286 reaction equation
[NH:1]1[C:5]2(CCCCC2)[CH:4]=CS1(=O)=O.Br[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[S:22](=[O:33])(=[O:32])[NH:23][C:24]3([CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]3)[C:25]=2[CH3:26])=[CH:17][CH:16]=1.C(N)C>C(O)C>[CH2:5]([NH:1][CH2:26][C:25]1[C:24]2([CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)[NH:23][S:22](=[O:33])(=[O:32])[C:21]=1[C:18]1[CH:19]=[CH:20][C:15]([CH3:14])=[CH:16][CH:17]=1)[CH3:4]

Participants

5

Reactant 3

HCID 6341EthylamineHCID 21910614HCID 21910614, compoundHCID 86591496HCID 86591496, compound

Product 1

HCID 21910639HCID 21910639, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Ethylaminomethyl-3-(4-methylphenyl)-2-thia-1-azaspiro[4.5]dec-3-ene 2,2-dioxide, shown below, was prepared according to the methods described in Examples 1 and 2. Bromination with N-bromosuccinimide afforded a mixture of 4-bromomethyl-3-4-methylphenyl)-2-thia-1-azaspiro[4.5]dec-3-ene 2,2-dioxide and 3-(4-bromomethyl-phenyl)-4-methyl-2-thia-1-azaspiro[4.5]dec-3-ene 2,2-dioxide. The raw mixture (400 mg) was dissolved in ethanol (10 mL) and ethylamine (70% in water, 5 mL) was added. The solution was stirred overnight at room temperature, concentrated and the residue was dissolved in CH2Cl2, washed with water and extracted with 0.5 M HCl. After addition of NaOH and extraction with CH2Cl2 the organic layer was dried (Na2SO4) and evaporated. The two products were separated by column chromatography (CH2Cl2/acetone 9:1) and the title compound compound [4-Ethylaminomethyl-3-(4-methylphenyl)-2-thia-1-azaspiro[4.5]dec-3-ene 2,2-dioxide] was isolated as white crystals. Yield: 80 mg, 24%; MS (IS): 334 [MH]+.

Workup

  1. concentrationconcentrated
  2. dissolutionthe residue was dissolved in CH2Cl2
  3. washwashed with water
  4. extractionextracted with 0.5 M HCl
  5. additionAfter addition of NaOH and extraction with CH2Cl2 the organic layer
  6. dry with materialwas dried (Na2SO4)
  7. customevaporated
  8. customThe two products were separated by column chromatography (CH2Cl2/acetone 9:1)

Sources & evidence

ORD record
ord-4989c4fb94094f5f8db7af26e955a3c2
Source dataset
uspto-grants-2006_10
Patent number
US07125840B2

Reaction notes

Loading…