3,4-Dimethylaniline → HCID 178503192, compound

HRID 901901Notes

Reaction equation

HRID 901901 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[CH3:9])[NH2:5].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH3:20][S:21][C:22]1[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][CH:23]=1.[Cl-].[NH4+]>C1COCC1>[CH3:1][C:2]1[CH:3]=[C:4]([NH:5][C:26]([C:25]2[CH:28]=[CH:29][C:22]([S:21][CH3:20])=[CH:23][CH:24]=2)=[NH:27])[CH:6]=[CH:7][C:8]=1[CH3:9]

Participants

6

Reactant 4

HCID 72483,4-DimethylanilineHCID 25517Ammonium ChlorideHCID 5909604-(Methylthio)benzonitrileHCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 178503192HCID 178503192, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3,4-dimethylaniline (10 g, 83 mmol) in THF (10 ml), lithium bis(trimethylsilyl)amide (20% in THF, 93 ml, 99 mmol) was added under stirring in nitrogen blanket for a period of 20 minutes followed by 4-methylthiobenzonitrile (12.31 g, 83 mmol) over a period of 10 min. After 1 hour the reaction mixture was poured over ammonium chloride solution (30%, 100 ml). The resultant mixture was extracted with ethyl acetate and washed with water, dried over anhydrous sodium sulphate. The ethyl acetate extract was concentrated to yield the title compound (19 g, yield 85.1%, mp 111-113° C., purity 99.1% by HPLC). 1H-NMR (CDCl3):δ 2.23-2.24 (d, 6H), 2.51 (s, 3H), 4.81 (bs, 2H, D2O exchangeable), 6.70-6.72 (m, 1H), 6.77 (s, 1H), 7.08-7.1 (d, 1H), 7.25-7.27 (d, 2H), 7.76-7.78 (d, 2H). MS m/z: 271.3 (M+).

Workup

  1. extractionThe resultant mixture was extracted with ethyl acetate
  2. washwashed with water
  3. dry with materialdried over anhydrous sodium sulphate
  4. extractionThe ethyl acetate extract
  5. concentrationwas concentrated

Sources & evidence

ORD record
ord-5e4c1f74967d43ac921fe777cae56105
Source dataset
uspto-grants-2008_04
Patent number
US07365069B2

Reaction notes

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