1-Hexanol → HCID 9864892, compound

HRID 1614658Notes

Reaction equation

HRID 1614658 reaction equation
[CH3:1][CH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]([CH3:12])[CH3:11])[C:5]=1[NH:13][C:14]([NH:16][S:17](Cl)(=[O:19])=[O:18])=[O:15])[CH3:3].[CH2:21]([OH:27])[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].C(N(CC)CC)C>C1COCC1>[CH2:21]([O:27][S:17](=[O:18])(=[O:19])[NH:16][C:14]([NH:13][C:5]1[C:6]([CH:10]([CH3:11])[CH3:12])=[CH:7][CH:8]=[CH:9][C:4]=1[CH:2]([CH3:3])[CH3:1])=[O:15])[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

5

Reactant 3

HCID 81031-HexanolHCID 8471TriethylamineHCID 10615554HCID 10615554, compound

Product 1

HCID 9864892HCID 9864892, compoundYield 25.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of [[[2,6-bis(1 methylethyl)phenyl]amino]carbonyl]sulfamoyl chloride (5.0 g, 15.7 mmoles) in 80 mL THF was added dropwise to a solution of n-hexanol (1.60 g, 15.7 mmoles) and excess triethylamine (~3 mL) in 150 mL THF at room temperature under an atmosphere of N2. This was stirred for 16 hours and then concentrated in vacuo. The residue was partitioned between IN HCl and EtOAc and the organic layer was dried with MgSO4, filtered, and evaporated to give an oily tan solid. Trituration with acetone/hexanes (9:1) gave 1.56 g of the title compound as a white solid, mp 148-151° C.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was partitioned between IN HCl and EtOAc
  3. dry with materialthe organic layer was dried with MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customto give an oily tan solid

Sources & evidence

ORD record
ord-904e982296e642768da51d3277669e66
Source dataset
uspto-grants-1993_03
Patent number
US05198466

Reaction notes

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