O-Toluidine → HCID 19427053, compound

HRID 1033077Notes

Reaction equation

HRID 1033077 reaction equation
[NH2:1][C:2]1[C:3]([CH3:8])=[CH:4][CH:5]=[CH:6][CH:7]=1.[C:9](OCC)(OCC)(OCC)[CH3:10].[CH:20]1([NH2:26])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1>C(O)(=O)C>[CH3:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:1][C:9](=[N:26][CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)[CH3:10]

Participants

6

Reactant 3

HCID 7242O-ToluidineHCID 7965Cyclohexylamine2×HCID 66221Triethyl orthoacetate

Product 1

HCID 19427053HCID 19427053, compoundYield 27.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
120 °C

Procedure

Glacial acetic acid (catalytic amount, 5 drops) was added to a mixture of o-toluidine (1.07 g, 10 mmol) and triethyl orthoacetate (1.94 g, 12 mmol) and was heated at 120° C. for 60 min. The reflux condenser was replaced by a distillation condenser and the low volatiles were distilled off at 74°-76° C. (head temperature) . The undistilled residue was dried under manifold vacuum to give a light yellow liquid. Now cyclohexyl amine (0.99 g, 10 mmol) followed by catalytic amount (0.1 ml) of glacial acetic acid was added and the resulting suspension was heated on oil bath at 140° C. for 12 hr. The reflux condenser was replaced by a distillation condenser and the low volatiles including unreacted cyclohexyl amine were removed under manifold vacuum (0.5 mm Hg). After it cooled to room temperature, dichloromethane (30 ml) was added and then it was washed with dil. sodium bicarbonate solution. The organic phase was dried over Na2SO4, filtered and concentrated to give an off-white solid. It was crystallized twice from 95 EtOH-H20 to give the title compound (0.636 g, 24%) as bright white needles. Mp 130°-31° C.

Workup

  1. customThe reflux condenser was replaced by a distillation condenser
  2. distillationthe low volatiles were distilled off at 74°-76° C. (head temperature)
  3. customThe undistilled residue was dried under manifold vacuum
  4. customto give a light yellow liquid
  5. additionwas added
  6. temperaturethe resulting suspension was heated on oil bath at 140° C. for 12 hr
  7. customThe reflux condenser was replaced by a distillation condenser
  8. customwere removed under manifold vacuum (0.5 mm Hg)
  9. temperatureAfter it cooled to room temperature
  10. additiondichloromethane (30 ml) was added
  11. washit was washed with dil. sodium bicarbonate solution
  12. dry with materialThe organic phase was dried over Na2SO4
  13. filtrationfiltered
  14. concentrationconcentrated
  15. customto give an off-white solid
  16. customIt was crystallized twice from 95 EtOH-H20

Sources & evidence

ORD record
ord-585ecf233252434da6ebcfdd6c212deb
Source dataset
uspto-grants-1994_05
Patent number
US05308869

Reaction notes

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