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

HRID 2297577Notes

Reaction equation

HRID 2297577 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 the title intermediate (120 mg, 72%).

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-89e54f21405e4e809bc63b6bbffd2a2b
Source dataset
uspto-grants-2002_12
Patent number
US06492372B1

Reaction notes

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