Tetrahydrofuran → HCID 178510063, compound

HRID 2243331Notes

Reaction equation

HRID 2243331 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[NH2:10])[C:5]#[N:6].O1CCCC1.C(N(CC)CC)C.C1C=[CH:25][C:26](=[O:39])[C:27]2C=1C(C(Cl)=O)=C1C=2C=CC=C1>ClCCl>[CH:26]([O:39][CH:8]([CH3:7])[CH3:9])([CH3:27])[CH3:25].[NH2:10][C:9]1[CH:8]=[CH:7][C:4]([C:5]#[N:6])=[CH:3][C:2]=1[NH-:1]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 7372853,4-DiaminobenzonitrileHCID 87540947Fluoren-4-one-9-carboxylic acid chloride

Product 2

HCID 7914Diisopropyl EtherHCID 178510063HCID 178510063, compoundYield 319.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The procedure used in stage 1 of Example 1 is followed, but starting from 2.4 g of 3,4-diaminobenzonitrile and 30 ml of tetrahydrofuran, 4.6 ml of triethylamine and 4 g of fluoren-4-one-9-carboxylic acid chloride in 115 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 formation of a paste with diisopropyl ether, in this way we obtain 3.8 g of (2-amino-5-cyanophenyl)amide of 9-oxo-9H-fluorene-4-carboxylic acid, in the form of a beige 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

Sources & evidence

ORD record
ord-fcd022c50c5d4980be6832eb0e0e25fa
Source dataset
uspto-grants-2010_03
Patent number
US07674795B2

Reaction notes

Loading…