Water → HCID 178460025, compound

HRID 482857Notes

Reaction equation

HRID 482857 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][CH2:10][C:11]2[N:12]3[N:18]=[C:17]([CH3:19])[CH:16]=[C:13]3[NH:14][N:15]=2)[CH:5]=[CH:6][CH:7]=1.[C:20](Cl)([CH:22]=[CH2:23])=[O:21].O.C(OCC)(=O)C>C(#N)C.CC(N(C)C)=O.N1C=CC=CC=1.[N+](C1C=CC=CC=1)([O-])=O>[C:20]([NH:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][CH2:10][C:11]2[N:12]3[N:18]=[C:17]([CH3:19])[CH:16]=[C:13]3[NH:14][N:15]=2)[CH:5]=[CH:6][CH:7]=1)(=[O:21])[CH:22]=[CH2:23]

Participants

9

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 13140Acryloyl chlorideHCID 178422368HCID 178422368, compound

Product 1

HCID 178460025HCID 178460025, compound

Reagents, catalysts & solvents 4

HCID 1049PyridineSolventHCID 6342AcetonitrileSolventHCID 7416NitrobenzeneSolventHCID 31374DimethylacetamideSolvent

Procedure

25.2 g (0.1 mol) of 3-[3-(3-aminophen yl)-propyl]-6-methyl-1H-pyrazolo[5,1-c]-1,2,4-triazole synthesized according to Preparation Example 9 described in Japanese Patent Application (OPI) No. 42045/83 corresponding to European Patent Application No. 0073636A1 was dissolved in a mixture of 200 ml of acetonitrile, 100 ml of dimethylacetamide, 16 ml of pyridine, and 1 ml of nitrobenzene. 9.5 g (0.105 mol) of acryl chloride was gradually added dropwise thereto, and, after reaction for one-hour at a temperature not higher than 10° C. with stirring, water and ethyl acetate were added thereto, followed by extracting procedure. The ethyl acetate phase was well washed with saturated sodium chloride aqueous solution, then the solvent was removed. The product was crystallized from acetonitrile. Recrystallization of the crude product from acetonitrile yielded 20.6 g of C-5 having m.p. of 195° to 197° C.

Workup

  1. customaccording to Preparation Example 9
  2. customafter reaction for one-hour at a temperature not higher than 10° C.
  3. extractionby extracting procedure
  4. washThe ethyl acetate phase was well washed with saturated sodium chloride aqueous solution
  5. customthe solvent was removed
  6. customThe product was crystallized from acetonitrile
  7. customRecrystallization of the crude product from acetonitrile
  8. customyielded 20.6 g of C-5 having m.p. of 195° to 197° C.

Sources & evidence

ORD record
ord-e3faca3561f64c028b7e550dcc7454a2
Source dataset
uspto-grants-1986_03
Patent number
US04576910

Reaction notes

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