Hydrochloric Acid → HCID 3525923, compound

HRID 1497083Notes

Reaction equation

HRID 1497083 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=O.[C:17]([CH2:19][C:20](OCC)=[O:21])#[N:18].O.O.O.O.O.O.O.[Cl-].[Ce+3].[Cl-].[Cl-].Cl>O>[Cl:8][C:5]1[CH:4]=[C:3]2[C:2](=[CH:7][CH:6]=1)[NH:1][C:20](=[O:21])[C:19]([C:17]#[N:18])=[C:9]2[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7764Ethyl cyanoacetateHCID 128702-Amino-5-chlorobenzophenoneHCID 21585214Cerium trichloride heptahydrate

Product 1

HCID 3525923HCID 3525923, compoundYield 32.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
200 °C

Procedure

A mixture of (2-amino-5-chlorophenyl)(phenyl)methanone (1 g, 4.32 mmol, Eq: 1.00), ethyl 2-cyanoacetate (2.44 g, 2.3 ml, 21.6 mmol, Eq: 5) and cerium (III) chloride heptahydrate (322 mg, 863 μmol, Eq: 0.2) was heated to 200° C. for 30 min in a microwave. Then water was added and the mixture was acidified to pH 2-3 with 0.1N HCl. The mixture was then extracted with ethyl acetate (3×) and the combined extracts were washed with water and brine, dried with Na2SO4, filtered and evaporated. The remaining residue was triturated with a mixture of DCM (5 ml) and heptane (2 ml) for 2 h. Filtration yielded the title compound (389 mg, light yellow solid). MS (ESI): 281.1 (M+H)+.

Workup

  1. extractionThe mixture was then extracted with ethyl acetate (3×)
  2. washthe combined extracts were washed with water and brine
  3. dry with materialdried with Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe remaining residue was triturated with a mixture of DCM (5 ml) and heptane (2 ml) for 2 h
  7. filtrationFiltration

Sources & evidence

ORD record
ord-1eb1b29ed86b4622b77c44eda75a229d
Source dataset
uspto-grants-2015_12
Patent number
US09199938B2

Reaction notes

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