2-Amino-2-methyl-1-propanol → 2,4-Difluoro-N-(2-hydroxy-1,1-dimethylethyl)benzamide

HRID 1934348Notes

Reaction equation

HRID 1934348 reaction equation
CCN=C=NCCCN(C)C.Cl.[F:13][C:14]1[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:15]=1[C:16]([OH:18])=O.[NH2:24][C:25]([CH3:29])([CH3:28])[CH2:26][OH:27].C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl>[OH:27][CH2:26][C:25]([NH:24][C:16](=[O:18])[C:15]1[CH:19]=[CH:20][C:21]([F:23])=[CH:22][C:14]=1[F:13])([CH3:29])[CH3:28]

Participants

6

Reactant 4

HCID 118072-Amino-2-methyl-1-propanolHCID 741022,4-Difluorobenzoic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 98374972,4-Difluoro-N-(2-hydroxy-1,1-dimethylethyl)benzamideYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

WSC HCl (7.68 g, 40 mmol) was added to a mixture of 2,4-difluorobenzoic acid (6.32 g, 40 mmol), 2-amino-2-methyl-1-propanol (3.56 g, 40 mmol) and HOBt (5.40 g, 40 mmol) in methylene chloride (150 ml), and stirred at room temperature for 3 hours. The reaction mixture was concentrated, diluted with ethyl acetate and washed with saturated aqueous NaHCO3, 1N hydrochloric acid, saturated aqueous NaHCO3 and brine, successively, dried over MgSO4 and concentrated under a reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate 3/1) to give the title compound (6.20 g; 68%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with ethyl acetate
  3. washwashed with saturated aqueous NaHCO3, 1N hydrochloric acid, saturated aqueous NaHCO3 and brine
  4. dry with materialsuccessively, dried over MgSO4
  5. concentrationconcentrated under a reduced pressure
  6. customThe residue was purified by silica gel chromatography (hexane/ethyl acetate 3/1)

Sources & evidence

ORD record
ord-cc229b0eff794dae81b4f610b40b4d68
Source dataset
uspto-grants-2002_05
Patent number
US06384033B1

Reaction notes

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