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

HRID 18050

Reaction equation

HRID 18050 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. customand purified by flash column chromatography (silica, hexane:EtOAc 3:1)

Sources & evidence

ORD record
ord-3f76a09bbda543c59ed468a1f6be2b70
Source dataset
uspto-grants-2010_06
Patent number
US07741328B2

Linked notes

Loading…