Diisopropylethylamine → HCID 18546488, compound

HRID 1267514Notes

Reaction equation

HRID 1267514 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][C:9]=1[NH2:17].C(N(C(C)C)C(C)C)C.[F:27][C:28]([F:46])([F:45])[C:29]1[CH:30]=[C:31]([C:39]([CH3:44])([CH3:43])[C:40](Cl)=[O:41])[CH:32]=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:34]=1>C(Cl)Cl>[F:27][C:28]([F:45])([F:46])[C:29]1[CH:30]=[C:31]([C:39]([CH3:43])([CH3:44])[C:40]([NH:17][C:9]2[CH:10]=[C:11]([N+:14]([O-:16])=[O:15])[CH:12]=[CH:13][C:8]=2[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[CH3:1])=[O:41])[CH:32]=[C:33]([C:35]([F:36])([F:37])[F:38])[CH:34]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 112671412-(3,5-Bis(trifluoromethyl)phenyl)-2-methylpropanoyl chlorideHCID 185464992'-Methyl-4-nitro-biphenyl-2-ylamine

Product 1

HCID 18546488HCID 18546488, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of 925 mg (4.05 mmol) 2′-methyl-4-nitro-biphenyl-2-ylamine and 1.03 ml (6.08 mmol) N-ethyldiisopropylamine in 9 ml CH2Cl2 was cooled in an ice bath and a solution of 1.42 g (4.46 mmol) 2-(3,5-bis-trifluoromethyl-phenyl)-2-methyl-propionyl chloride in 1 ml CH2Cl2 was added dropwise. The reaction mixture was kept at room temperature for 2 hrs. After addition of CH2Cl2, the organic layer washed with 1 N NaOH solution and 1 N HCl solution, dried (MgSO4) and evaporated to give 1.84 g (89%) 2-(3,5-bis-trifluoromethyl-phenyl)-N-(2′-methyl-4-nitro-biphenyl-2-yl)-isobutyramide as yellow crystals, MS (ISP): 511.3 (M+H)+.

Workup

  1. washthe organic layer washed with 1 N NaOH solution and 1 N HCl solution
  2. dry with materialdried (MgSO4)
  3. customevaporated

Sources & evidence

ORD record
ord-f41934072b70478b85eb0e6bc177be53
Source dataset
uspto-grants-2003_04
Patent number
US06552088B2

Reaction notes

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