Triethylamine → (2-Amino-4-trifluoromethoxyphenyl)amide

HRID 2243329Notes

Reaction equation

HRID 2243329 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]([F:12])([F:11])[F:10])=[CH:4][C:3]=1[NH2:13].C(N(CC)CC)C.C1C=[CH:23][C:24](=[O:37])[C:25]2C=1C(C(Cl)=O)=C1C=2C=CC=C1>ClCCl>[CH:2]([O:37][CH:24]([CH3:23])[CH3:25])([CH3:7])[CH3:3].[NH2:13][C:3]1[CH:4]=[C:5]([O:8][C:9]([F:10])([F:11])[F:12])[CH:6]=[CH:7][C:2]=1[NH-:1]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27739594-(Trifluoromethoxy)benzene-1,2-diamineHCID 87540947Fluoren-4-one-9-carboxylic acid chloride

Product 2

HCID 7914Diisopropyl EtherHCID 86621031(2-Amino-4-trifluoromethoxyphenyl)amideYield 97.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The procedure used in stage 1 of Example 1 is followed, but starting from 1 g of 1,2-diamino-4-(trifluoromethoxy)benzene, 1.3 ml of triethylamine and 1.15 g of fluoren-4-one-9-carboxylic acid chloride in 30 ml of dichloromethane. After stirring for 20 hours at room temperature, the precipitate that formed is filtered off, and washed with dichloromethane, with water, and then with a 10% saturated aqueous solution of sodium hydrogen carbonate and, finally, with water. After drying and formation of a paste with diisopropyl ether, in this way we obtain 485 mg of (2-amino-4-trifluoromethoxyphenyl)amide of 9-oxo-9H-fluorene-4-carboxylic acid, in the form of a yellow powder, which is used as it is in the following stage, with the following characteristics:

Workup

  1. customthe precipitate that formed
  2. filtrationis filtered off
  3. washwashed with dichloromethane, with water
  4. customAfter drying

Sources & evidence

ORD record
ord-a6bb55ee8db14c528feb4c4249da5423
Source dataset
uspto-grants-2010_03
Patent number
US07674795B2

Reaction notes

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