2,4-Dichlorobenzaldehyde → HCID 135844972, compound

HRID 1951556Notes

Reaction equation

HRID 1951556 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([Cl: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]([Cl: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 134042,4-DichlorobenzaldehydeHCID 5325263(2Z)-3-Amino-2-butenenitrileHCID 179309881-(4-Methyl-1,3-thiazol-2-yl)propan-2-one

Product 1

HCID 135844972HCID 135844972, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

150 mg (0.857 mmol) of 2,4-dichlorobenzaldehyde, 133 mg (0.857 mmol) of the compound from example 4A and 70 mg (0.857 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, and the crude product is taken up in 3 ml of ethyl acetate. The crystallizing solid is removed by filtration. The product obtained in this way is washed with a little diethyl ether. 85 mg (26% of theory) of the title compound are obtained.

Workup

  1. customthe volatile components are removed in a rotary evaporator
  2. customThe crystallizing solid is removed by filtration
  3. customThe product obtained in this way
  4. washis washed with a little diethyl ether

Sources & evidence

ORD record
ord-f55386ee9f29460994ba0416718ce476
Source dataset
uspto-grants-2013_03
Patent number
US08404723B2

Reaction notes

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