Water → N-[10-[4-(1H-Imidazol-1-yl)phenoxy]decyl]-2-naphthalenesulfonamide

HRID 1417326Notes

Reaction equation

HRID 1417326 reaction equation
[N:1]1([C:6]2[CH:23]=[CH:22][C:9]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][NH2:21])=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.C(N(CC)CC)C.[CH:31]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:34]=[CH:33][C:32]=1[S:41](Cl)(=[O:43])=[O:42].O>C(OCC)C.C(O)C>[N:1]1([C:6]2[CH:23]=[CH:22][C:9]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][NH:21][S:41]([C:32]3[CH:33]=[CH:34][C:35]4[C:40](=[CH:39][CH:38]=[CH:37][CH:36]=4)[CH:31]=3)(=[O:43])=[O:42])=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

7

Reactant 4

HCID 962WaterHCID 71252-Naphthalenesulfonyl chlorideHCID 8471TriethylamineHCID 5441526510-[4-(1H-Imidazol-1-yl)phenoxy]decaneamine

Product 1

HCID 67598097N-[10-[4-(1H-Imidazol-1-yl)phenoxy]decyl]-2-naphthalenesulfonamide

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A suspension of 2.5 g of 10-[4-(1H-imidazol-1-yl)phenoxy]decaneamine (Example 66) in 250 ml of diethyl ether containing 3 ml of triethylamine is stirred while 2.0 g of 2-naphthalenesulfonylchloride is added. The reaction mixture is stirred at room temperature for 72 hours and 50 ml of H2O added. The solvents are decanted, leaving a viscous solid. The solid is dissolved in 100 ml of 50% aqueous ethanol. Careful concentration under a gentle stream of air gives a crystalline solid. The solid is collected washed with water and dried in vacuo at room temperature; m.p. 112°-115° C.; yield, 0.2 g.

Workup

  1. additionis added
  2. customThe solvents are decanted
  3. customleaving a viscous solid
  4. concentrationCareful concentration under a gentle stream of air
  5. customgives a crystalline solid
  6. customThe solid is collected
  7. washwashed with water
  8. customdried in vacuo at room temperature
  9. customyield

Sources & evidence

ORD record
ord-2260ccf9c03040fc8ebfbf9f161255e8
Source dataset
uspto-grants-1999_03
Patent number
US05877196

Reaction notes

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