2-Amino-2-methyl-1-propanol → N-(2-hydroxy-1,1-dimethylethyl)-2-biphenylcarboxamide

HRID 27244

Reaction equation

HRID 27244 reaction equation
[C:1]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:2]([C:7]([OH:9])=O)=[CH:3][CH:4]=[CH:5][CH:6]=1.S(Cl)(Cl)=O.[NH2:20][C:21]([CH3:25])([CH3:24])[CH2:22][OH:23]>C(Cl)Cl>[OH:23][CH2:22][C:21]([NH:20][C:7]([C:2]1[C:1]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:9])([CH3:25])[CH3:24]

Participants

5

Reactant 3

HCID 118072-Amino-2-methyl-1-propanolHCID 24386Thionyl ChlorideHCID 70357o-Phenylbenzoic acid

Product 1

HCID 11054714N-(2-hydroxy-1,1-dimethylethyl)-2-biphenylcarboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

6 Parts of biphenyl-2-carboxylic acid is added to 15 parts by volume of thionyl chloride and the mixture is stirred at ambient temperature for about 22 hours. The thionyl chloride is distilled off under reduced pressure, then benzene is added and distilled off under reduced pressure leaving an oil. The oil is dissolved in 15 parts by volume of methylene chloride and added dropwise with stirring to a solution of 5.5 parts of 2-amino-2-methylpropanol in 15 parts by volume of methylene chloride at 0° C. The resultant mixture is stirred at ambient temperature overnight, filtered and the filtrate washed with water, twice with 25 parts by volume of 5% hydrochloric acid, twice with 25 parts by volume of 5% sodium hydroxide, and water. The filtrate is then dried over anhydrous magnesium sulfate and the solvent removed under reduced pressure to give N-(2-hydroxy-1,1-dimethylethyl)-2-biphenylcarboxamide, as white crystals, melting at about 72.5°-74° C. after recrystallization from ether.

Workup

  1. distillationThe thionyl chloride is distilled off under reduced pressure
  2. additionbenzene is added
  3. distillationdistilled off under reduced pressure
  4. customleaving an oil
  5. additionadded dropwise
  6. filtrationfiltered
  7. washthe filtrate washed with water, twice with 25 parts by volume of 5% hydrochloric acid, twice with 25 parts by volume of 5% sodium hydroxide, and water
  8. dry with materialThe filtrate is then dried over anhydrous magnesium sulfate
  9. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-17abaf210f7c49818746136729f9f469
Source dataset
uspto-grants-1980_09
Patent number
US04220778

Linked notes

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