Methane → 2-Cyanomethoxy-5-(1,1-dimethylethyl)benzenamine

HRID 126746Notes

Reaction equation

HRID 126746 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:5]=[CH:4][C:3]=1[OH:12].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:20][C:21]#[N:22].C>CC(C)=O.CCCCCC.C(OCC)(=O)C>[C:21]([CH2:20][O:12][C:3]1[CH:4]=[CH:5][C:6]([C:8]([CH3:9])([CH3:11])[CH3:10])=[CH:7][C:2]=1[NH2:1])#[N:22]

Participants

8

Reactant 4

HCID 297MethaneHCID 7856Chloroacetonitrile2×HCID 11430Potassium Carbonate2×HCID 709822-Amino-4-tert-butylphenol

Product 1

HCID 128734142-Cyanomethoxy-5-(1,1-dimethylethyl)benzenamine

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Amino-4-(1,1dimethylethyl)phenol (90.0 g, 546 mol, described in Example 1) was dissolved in acetone (900 ml) and heated at reflux for 2 days in the presence of anhydrous potassium carbonate (81.0 g, 534 mmol) and chloroacetonitrile (40.5 g, 535 mmol). The mixture was allowed to stand for an additional day at 20°-24° C. The mixture then was treated with more potassium carbonate (15.0 g) and chloroacetonitrile (10 g) under the same conditions. The mixture was mixed with charcoal and filtered through diatomaceous earth. The filtrate was evaporated to afford a residue which, when dissolved in hexane containing a small amount of ethyl acetate, afforded tan crystals of the title compound; Anal. Calc'd for C12H16N2O: C, 70.56%; H, 7.90%; N, 13.72%; Found: C, 70.60% H, 8.00%; N, 13.85%; IR(CHCl3) 3460, 3380, 2240, 1620, 1515, 1166, cm-1 ; NMR(CDCl3) δ 1.3 (s, 9H), 3.7 (s,2H), 4.7 (s,2H), 6.75 (s, 3H).

Workup

  1. temperatureheated
  2. waitto stand for an additional day at 20°-24° C
  3. filtrationfiltered through diatomaceous earth
  4. customThe filtrate was evaporated
  5. customto afford a residue which, when

Sources & evidence

ORD record
ord-036c9dea9e9e42179377083089b42b3c
Source dataset
uspto-grants-1981_03
Patent number
US04254121

Reaction notes

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