Water → HCID 58226704, compound

HRID 2364780Notes

Reaction equation

HRID 2364780 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][CH2:10][C:11]([C:13]2[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][CH:14]=2)=O)=[CH:4][CH:3]=1.[C:21]([C:25]1[CH:31]=[CH:30][C:28]([NH2:29])=[CH:27][CH:26]=1)([CH3:24])([CH3:23])[CH3:22].C(O)(C(F)(F)F)=O.O>C1(C)C=CC=CC=1.C(OCC)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:29]([C:28]3[CH:30]=[CH:31][C:25]([C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:26][CH:27]=3)[C:11]([C:13]3[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][CH:14]=3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 698614-Tert-ButylanilineHCID 2192171,4-Bis(4-bromophenyl)-1,4-butanedione

Product 1

HCID 58226704HCID 58226704, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of the product from Example 26E (4.00 g, 10.10 mmol) in toluene (40 mL) was added 4-tert-butylaniline (1.81 g, 12.12 mmol) followed by TFA (2.30 g, 20.20 mmol). Mixture heated to 110° C. for 2 h. Mixture cooled to room temperature and water and diethyl ether were added. Stirred for 15 min, filtered, washed with water and diethyl ether and dried to provide the title compound as a white solid (4.61 g; 90% yield).

Workup

  1. temperatureMixture cooled to room temperature
  2. filtrationfiltered
  3. washwashed with water and diethyl ether
  4. customdried

Sources & evidence

ORD record
ord-bfa695d235094b5ba3f52498f7af8839
Source dataset
uspto-grants-2014_04
Patent number
US08691938B2

Reaction notes

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