Toluene → 5-(4-tert-Butyl-cyclohexyloxy)-2-methyl-benzothiazole

HRID 2404190Notes

Reaction equation

HRID 2404190 reaction equation
[CH3:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:5]=2[N:6]=1.[C:12]([C@@H:16]1[CH2:21][CH2:20][C@H:19](O)[CH2:18][CH2:17]1)([CH3:15])([CH3:14])[CH3:13].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(C)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>>[C:12]([CH:16]1[CH2:21][CH2:20][CH:19]([O:11][C:8]2[CH:9]=[CH:10][C:4]3[S:3][C:2]([CH3:1])=[N:6][C:5]=3[CH:7]=2)[CH2:18][CH2:17]1)([CH3:15])([CH3:14])[CH3:13]

Participants

6

Reactant 5

HCID 1140TolueneHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 6997992-Methyl-1,3-benzothiazol-5-olHCID 178445811HCID 178445811, compound

Product 1

HCID 669265855-(4-tert-Butyl-cyclohexyloxy)-2-methyl-benzothiazole

Procedure

2-Methyl-benzothiazol-5-ol (2.5 g, 0.015 mol), cis-4-tert-butylcyclohexanol (2.84 g, 0.0182 mol), and Triphenylphosphine (4.76 g, 0.0182 mol) were combined in dry Toluene (100 mL, 1 mol) and stirred under nitrogen. Diisopropyl azodicarboxylate (3.6 mL, 0.018 mol) was added dropwise. The reaction was then stirred at RT overnight. Reaction was then concentrated to dryness and then residue was dissolved in DCM and 5 g of SiO2 was added. Solvent was removed under reduced pressure and resulting powder was loaded onto a 40 g column and purified via column chromatography using a gradient of 0-60% EtOAC/Hexanes.

Workup

  1. stirringThe reaction was then stirred at RT overnight
  2. customReaction
  3. concentrationwas then concentrated to dryness
  4. dissolutionresidue was dissolved in DCM
  5. addition5 g of SiO2 was added
  6. customSolvent was removed under reduced pressure
  7. customresulting powder
  8. custompurified via column chromatography

Sources & evidence

ORD record
ord-32ebcaad2efd46a68a791b8ed3ac0d7f
Source dataset
uspto-grants-2014_08
Patent number
US08802659B2

Reaction notes

Loading…