2-Chloro-4-fluorobenzaldehyde → HCID 135844967, compound

HRID 1951550Notes

Reaction equation

HRID 1951550 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[CH3:11][C:12]1[N:13]=[C:14]([CH2:17][C:18]([CH3:20])=O)[S:15][CH:16]=1.[NH2:21]/[C:22](/[CH3:26])=[CH:23]\[C:24]#[N:25]>C(O)(C)C>[Cl:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH:4]1[C:17]([C:14]2[S:15][CH:16]=[C:12]([CH3:11])[N:13]=2)=[C:18]([CH3:20])[NH:21][C:22]([CH3:26])=[C:23]1[C:24]#[N:25]

Participants

5

Reactant 3

HCID 1450242-Chloro-4-fluorobenzaldehydeHCID 5325263(2Z)-3-Amino-2-butenenitrileHCID 179309881-(4-Methyl-1,3-thiazol-2-yl)propan-2-one

Product 1

HCID 135844967HCID 135844967, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

150 mg (0.946 mmol) of 2-chloro-4-fluorobenzaldehyde, 147 mg (0.811 mmol) of the compound from example 4A and 78 mg (0.811 mmol) of 3-aminocrotononitrile are dissolved in 4 ml of isopropanol and stirred at the reflux temperature overnight. After cooling to room temperature, the volatile components are removed in a rotary evaporator, the crude material is taken up in 5 ml of ethyl acetate, and the precipitated product is then filtered off 199 mg (58% of theory) of the title compound are obtained.

Workup

  1. customthe volatile components are removed in a rotary evaporator
  2. filtrationthe precipitated product is then filtered off 199 mg (58% of theory) of the title compound
  3. customare obtained

Sources & evidence

ORD record
ord-4a25b0c092ab4240bb5f9b5149ae94eb
Source dataset
uspto-grants-2013_03
Patent number
US08404723B2

Reaction notes

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