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

HRID 1072465Notes

Reaction equation

HRID 1072465 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-293138e43a5a4a4fb8f65182028fcdb1
Source dataset
uspto-grants-2005_06
Patent number
US06911439B2

Reaction notes

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