4-Benzoylbenzoic acid → HCID 10297752, compound

HRID 646192Notes

Reaction equation

HRID 646192 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([C:7]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([OH:17])=O)=[CH:11][CH:10]=2)=[O:8])=[CH:3][CH:2]=1.Cl.CN(C)CCCN=C=NCC.C(N(C(C)C)C(C)C)C.[NH2:39][C:40]([CH3:55])([CH2:43][O:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=1[C:51]([F:54])([F:53])[F:52])[C:41]#[N:42]>ClCCl.CN(C)C1C=CN=CC=1>[C:7]([C:9]1[CH:10]=[CH:11][C:12]([C:15]([NH:39][C:40]([C:41]#[N:42])([CH3:55])[CH2:43][O:44][C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=2[C:51]([F:53])([F:54])[F:52])=[O:17])=[CH:13][CH:14]=1)(=[O:8])[C:4]1[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 691474-Benzoylbenzoic acidHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 17989731HCID 17989731, compound

Product 1

HCID 10297752HCID 10297752, compoundYield 66.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

330 mg of benzophenone-4-carboxylic acid are dissolved in 6 ml of dichloromethane, then 283 mg of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride, 18 mg of 4-dimethylaminopyridine and 222 mg of ethyldiisopropylamine are added, and stirred for 20 minutes at room temperature. 300 mg of 2-amino-2-methyl-3-(2-trifluoromethylphenoxy)-propionitrile are subsequently added, and the mixture stirred for a further 40 hours. Afterwards, the mixed solution is washed with an aqueous sodium bicarbonate solution, then with a 1 n hydrochloric acid solution and finally with a saturated sodium chloride solution. The organic phase is then separated, dried with sodium sulphate, filtered and concentrated by evaporation. After recrystallisation in diethylether, the residue yields 372 mg of the title compound with a melting point of 121-123° C.

Workup

  1. stirringthe mixture stirred for a further 40 hours
  2. washAfterwards, the mixed solution is washed with an aqueous sodium bicarbonate solution
  3. customThe organic phase is then separated
  4. dry with materialdried with sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated by evaporation
  7. customAfter recrystallisation in diethylether

Sources & evidence

ORD record
ord-c062c66670864639ae15ccc55eb7fe52
Source dataset
uspto-grants-2010_04
Patent number
US07705044B2

Reaction notes

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