Tert-Butylamine → HCID 10866848, compound

HRID 2258274Notes

Reaction equation

HRID 2258274 reaction equation
[C:1]1([CH3:9])[C:2]([CH:7]=O)=[CH:3][CH:4]=[CH:5][CH:6]=1.[C:10]([NH2:14])([CH3:13])([CH3:12])[CH3:11]>C1(C)C=CC=CC=1>[CH3:9][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]=[N:14][C:10]([CH3:13])([CH3:12])[CH3:11]

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 107222-Methylbenzaldehyde

Product 1

HCID 10866848HCID 10866848, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A stirred solution of o-tolualdehyde (25 g, 0.21 mol), and t-butylamine (27.75 g, 0.38 mol) in toluene (250 mL) was refluxed under standard Dean-Stark conditions for 20 h. The solution was evaporated to an oil which was vacuum distilled (bp 70°-73° C., 0.6 mm Hg) to afford 33.9 g (93%) of product: IR (neat) 2980, 1645, 1605, 1460, 1375, 1210, 960, 910 cm-1 ; 1H NMR (400 MHz, CDCl3) δ 8.56 (s, 1 H), 7.86-7.83 (m, 1 H), 7.25-7.11 (m, 3 H), 2.46 (s, 3 H), 1.30 (s, 9 H); 13C NMR (CDCl3, 100 MHz) δ 153.7, 137.1, 135.1, 130.5, 129.6, 127.1, 126.4, 57.5, 29.8, 19.2; GC RT 7.6 min (DB-1, 30 m×0.53 mm, program: 100° C. for 5 min, 100°-260° C. at 15° C./min, hold at 260° C. for 12 min).

Workup

  1. customThe solution was evaporated to an oil which
  2. distillationdistilled (bp 70°-73° C., 0.6 mm Hg)

Sources & evidence

ORD record
ord-bee8370d2a8a43d0bf399e1cdeb29f59
Source dataset
uspto-grants-1997_08
Patent number
US05659084

Reaction notes

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