Tert-Butylamine → N-tert.butyl-alpha-phenyl-o-toluamide

HRID 1729681Notes

Reaction equation

HRID 1729681 reaction equation
[C:1]1([CH2:7][C:8]2[C:9]([C:14]([OH:16])=O)=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)(Cl)=O.[C:21]([NH2:25])([CH3:24])([CH3:23])[CH3:22]>C(OCC)C.N1C=CC=CC=1>[C:21]([NH:25][C:14]([C:9]1[C:8]([CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:16])([CH3:24])([CH3:23])[CH3:22]

Participants

6

Reactant 3

HCID 6385Tert-ButylamineHCID 11924o-Benzylbenzoic acidHCID 24386Thionyl Chloride

Product 1

HCID 20385869N-tert.butyl-alpha-phenyl-o-toluamide

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 3283Diethyl EtherSolvent3×

Procedure

To a mixture of 49.8 g. (0.235 mole) α-phenyl-o-toluic acid, 300 ml. ether and 10 ml. pyridine, add dropwise with stirring 25 ml. (0.35 mole) of thionyl chloride. The resulting mixture is stirred 21 hours at room temperature then filtered and the solvent removed in vacuo. The resulting acid chloride is dissolved in 150 ml. ether and added dropwise to 35.7 g (0.48 mole) of tert.butylamine in 500 ml. of ethyl ether, and the mixture cooled to 0° C. After addition is complete the resulting mixture is stirred 1 hour at room temperature, the layers separated, the ether washed with 100 ml. of water, 100 ml. of 2N sodium hydroxide and then with water again, dried over magnesium sulfate, filtered and evaporated to give N-tert.butyl-α-phenyl-o-toluamide; m.p. 91°- 92° C.

Workup

  1. additionTo a mixture of 49.8 g
  2. stirringThe resulting mixture is stirred 21 hours at room temperature
  3. filtrationthen filtered
  4. customthe solvent removed in vacuo
  5. dissolutionThe resulting acid chloride is dissolved in 150 ml
  6. additionAfter addition
  7. stirringis stirred 1 hour at room temperature
  8. customthe layers separated
  9. washthe ether washed with 100 ml
  10. dry with materialof 2N sodium hydroxide and then with water again, dried over magnesium sulfate
  11. filtrationfiltered
  12. customevaporated

Sources & evidence

ORD record
ord-3a239a4c46a74a16b0ec5dc01fcf9613
Source dataset
uspto-grants-1976_11
Patent number
US03989704

Reaction notes

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