Azobisisobutyronitrile → (2-(Naphthalene-1-yl)ethyl)(octyl)sulfane

HRID 1486136Notes

Reaction equation

HRID 1486136 reaction equation
[CH:1]([C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1)=[CH2:2].[CH2:13]([SH:21])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].N(C(C)(C)C#N)=NC(C)(C)C#N>>[C:3]1([CH2:1][CH2:2][S:21][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 81441-OctanethiolHCID 700041-Vinylnaphthalene

Product 1

HCID 118389705(2-(Naphthalene-1-yl)ethyl)(octyl)sulfane

Conditions

Temperature
110 °C

Procedure

5.0 grams (32.4 mmol, MW: 154.21) 1-vinylnaphthalene, 7.1 grams (48.6 mmol, MW: 146.29) octanethiol and 0.266 grams (1.62 mmol, MW: 164.21) 2,2′-azobis(2-methylpropionitrile) (AIBN) were charged in a 25 milliliter thick sealed glass reactor. After addition, the reaction mixture was stirred for 68 hours at 110° C. The reaction was then stopped and cooled down to room temperature. The excess of unreacted octanethiol was removed by air bath oven at 200° C. under vacuum for 1 hour. The final product was determined by IR, 1HNMR. Yield: 8.8 grams (90%). IR: (cm−1) 30045, 2924, 2853, 1596, 1510, 1459, 1394, 1377, 1261, 1219, 1165, 1016, 779, 730. 1H NMR (CDCl3): 8.03-7.33 (7H, m), 3.32 (2H, t), 2.91 (2H, t), 2.55 (2H, t), 1.57 (2H, m) 1.46-1.27 (10H, m), 0.87 (3H, t).

Workup

  1. customthick sealed glass reactor
  2. additionAfter addition
  3. temperaturecooled down to room temperature
  4. customThe excess of unreacted octanethiol was removed by air bath oven at 200° C. under vacuum for 1 hour

Sources & evidence

ORD record
ord-3fcf0d22ae29459bb4b2faa26a1c5105
Source dataset
uspto-grants-2016_08
Patent number
US09422499B2

Reaction notes

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