Potassium Iodide → 3-(4-{5-[(Propan-2-yl)sulfanyl]-1H-tetrazol-1-yl}phenoxy)propan-1-ol

HRID 1821970Notes

Reaction equation

HRID 1821970 reaction equation
[CH:1]([S:4][C:5]1[N:9]([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)[N:8]=[N:7][N:6]=1)([CH3:3])[CH3:2].Br[CH:18]([OH:21])[CH2:19][CH3:20].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(C)=O>[CH:1]([S:4][C:5]1[N:9]([C:10]2[CH:11]=[CH:12][C:13]([O:16][CH2:20][CH2:19][CH2:18][OH:21])=[CH:14][CH:15]=2)[N:8]=[N:7][N:6]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 12887879BromopropanolHCID 24383471HCID 24383471, compound

Product 1

HCID 685399363-(4-{5-[(Propan-2-yl)sulfanyl]-1H-tetrazol-1-yl}phenoxy)propan-1-ol

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

400 mg of 4-(5-isopropylsulfanyl-tetrazol-1-yl)-phenol, 471 mg of bromopropanol, 473 mg of potassium carbonate and 10 mg of potassium iodide are stirred for 15 hours at reflux in 10 ml of acetone. The reaction mixture is filtered and concentrated. The residue is taken up in ethyl acetate, washed with water and concentrated. Purification over silica gel yields 3-[4-(5-isopropylsulfanyl-tetrazol-1-yl)-phenoxy]-propan-1-ol. 1H-NMR (CDCl3) 300 MHz: 1.50 (d, 6H), 2.09 (m, 2H), 3.90 (t, 2H), 4.12 (m, 1H), 4.19 (t, 2H), 7.03 (d, 2H), 7.43 (d, 2H)

Workup

  1. filtrationThe reaction mixture is filtered
  2. concentrationconcentrated
  3. washwashed with water
  4. concentrationconcentrated
  5. customPurification over silica gel

Sources & evidence

ORD record
ord-1fe702f1e0a54f029f30a1ee015cdb21
Source dataset
uspto-grants-2009_10
Patent number
US07608631B2

Reaction notes

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