Tert-Butylamine → N-tert-butyl-2-fluoro-3-methylbenzamide

HRID 1878405Notes

Reaction equation

HRID 1878405 reaction equation
[F:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[CH3:12][C:13]([NH2:16])([CH3:15])[CH3:14].C(N(CC)CC)C.CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O>ClCCl.C(=O)([O-])O.[Na+]>[C:13]([NH:16][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][CH:9]=[C:10]([CH3:11])[C:2]=1[F:1])([CH3:15])([CH3:14])[CH3:12]

Participants

7

Reactant 4

HCID 6385Tert-ButylamineHCID 8471TriethylamineHCID 111923Propylphosphonic anhydrideHCID 27373792-Fluoro-3-methylbenzoic acid

Product 1

HCID 66878265N-tert-butyl-2-fluoro-3-methylbenzamideYield 54.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

To a stirred solution of 2-fluoro-3-methylbenzoic acid (8.76 mmol, 1.35 g), 2-methylpropan-2-amine (9.43 mmol, 1 mL, 0.690 g) and triethylamine (28.7 mmol, 4 mL, 2.90 g) in dichloromethane (20 mL) was added 1-propanephosphonic acid cyclic anhydride (13.50 mmol, 8 mL, 8.59 g, 50% solution in ethyl acetate). The reaction was stirred for 2 hours and diluted with dichloromethane and aqueous sodium hydrogen carbonate. The organic layer was separated, dried and concentrated under reduced pressure to yield the title compound (1 g).

Workup

  1. customThe organic layer was separated
  2. customdried
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-065c4144afaf48aa885dcc3fab227e8a
Source dataset
uspto-grants-2012_11
Patent number
US08314091B2

Reaction notes

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