Acetic Acid → 2,4-Diisopropyldibenzo[b,d]thiophen-3-amine

HRID 1750927Notes

Reaction equation

HRID 1750927 reaction equation
[CH2:1]=[C:2]([C:4]1[C:16]([NH2:17])=[C:15]([C:18]([CH3:20])=[CH2:19])[C:7]2[S:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:6]=2[CH:5]=1)[CH3:3].C(O)(=O)C>C(O)C.[Pd].[Pt]>[CH:2]([C:4]1[C:16]([NH2:17])=[C:15]([CH:18]([CH3:20])[CH3:19])[C:7]2[S:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:6]=2[CH:5]=1)([CH3:3])[CH3:1]

Participants

6

Reactant 2

HCID 176Acetic AcidHCID 584009962,4-Di(prop-1-en-2-yl)dibenzo[b,d]thiophen-3-amine

Product 1

HCID 584010202,4-Diisopropyldibenzo[b,d]thiophen-3-amineYield 82.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 23939PlatinumCatalystHCID 702EthanolSolvent

Procedure

2,4-di(prop-1-en-2-yl)dibenzo[b,d]thiophen-3-amine (9 g, 32.2 mmol) was dissolved in ethanol (150 mL) and 9 mL of acetic acid was added. To the flask, 10% Pd/C (9.0 g) and 5% Pt/C (9.0 g) were added and hydrogenated at 40 psi of H2 for over night. GC indicated complete conversion of olefin to alkane. The reaction mixture was filtered through a Celite pad and washed with methylene chloride. The filtrate was concentrated to produce 7.5 g (82%) of desired product.

Workup

  1. filtrationThe reaction mixture was filtered through a Celite pad
  2. washwashed with methylene chloride
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-6a8ff5cd09da47dfbc4945be2f774ac0
Source dataset
uspto-grants-2015_10
Patent number
US09156870B2

Reaction notes

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