Dihexylamine → 4-(N,N-di-n-hexylamino)-3-ethoxy-1,1-dioxo-1,2,5-thiadiazole

HRID 1070443Notes

Reaction equation

HRID 1070443 reaction equation
[CH2:1]([NH:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[CH2:14]([O:16][C:17]1[C:21](OCC)=[N:20][S:19](=[O:26])(=[O:25])[N:18]=1)[CH3:15]>C(O)C>[CH2:8]([N:7]([C:21]1[C:17]([O:16][CH2:14][CH3:15])=[N:18][S:19](=[O:26])(=[O:25])[N:20]=1)[CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

4

Reactant 2

HCID 8920DihexylamineHCID 112179953,4-Diethoxy-1,2,5-thiadiazole-1,1-dioxide

Product 1

HCID 221387874-(N,N-di-n-hexylamino)-3-ethoxy-1,1-dioxo-1,2,5-thiadiazoleYield 72.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Dihexylamine (90 mg, 0.48 mmol) was added to a solution of 3,4-diethyloxy-1,1-dioxo-1,2,5-thiadiazole (100 mg, 0.48 mmol) in ethanol (5 mL) and the reaction stirred overnight at room temperature. The solvent was removed under reduced pressure and the residue absorbed onto silica gel, and purified by flash column chromatography (silica, hexane:EtOAc 3:1) to yield 4-(N,N-di-n-hexylamino)-3-ethoxy-1,1-dioxo-1,2,5-thiadiazole (120 mg, 72%). MS (EI, m/e 345).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue absorbed onto silica gel
  3. custompurified by flash column chromatography (silica, hexane:EtOAc 3:1)

Sources & evidence

ORD record
ord-4b9312f0618d4a37908a288d1453df9a
Source dataset
uspto-grants-2005_06
Patent number
US06903088B2

Reaction notes

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