Acetylacetone → HCID 15725413, compound

HRID 1493533Notes

Reaction equation

HRID 1493533 reaction equation
[NH2:1][C:2]1[C:6]([C:7]#[N:8])=[C:5]([S:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[NH:4][N:3]=1.[CH3:17][C:18](=O)[CH2:19][C:20](=O)[CH3:21]>CC(O)=O>[CH2:10]([S:9][C:5]1[C:6]([C:7]#[N:8])=[C:2]2[N:1]=[C:18]([CH3:17])[CH:19]=[C:20]([CH3:21])[N:3]2[N:4]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 31261AcetylacetoneHCID 178510494HCID 178510494, compound

Product 1

HCID 15725413HCID 15725413, compoundYield 95.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A slurry of 0.5 g (2.2 mmole) of 3-amino-5-benzylthio-4-cyanopyrazole in 15 ml glacial HOAc was stirred at room temperature as 0.44 g (4.4 mmole) of 2,4-pentanedione was added. The mixture was stirred at room temperature for 3 hours. The white solid was collected by filtration, washed with HOAc, and dried to give 0.62 g (95.4 percent) of product as a white powder, m.p. 140° C. The analytical sample was recrystallized from 2-propanol. 1H NMR (DMSO-d-6): 7.5 (m, 2H, benzene), 7.3 (m, 3H, benzene), 7.1 (s, 1H, pyrazolopyrimidinyl H-6), 4.5 (s, 2H, CH2), 2.7 (s, 3H, CH3), 2.5 (s obscured by DMSO, 3H, CH3). 13C NMR (DMSO-d-6): 163.3, 155.3, 150.5, 146.7, 137.0, 129.1, 128.3, 127.3 112.8, 111.1, 79.0, 34.5, 24.1, 16.3. IR (KBr): 2220, 1615, 1550 cm -1.

Workup

  1. additionwas added
  2. filtrationThe white solid was collected by filtration
  3. washwashed with HOAc
  4. customdried

Sources & evidence

ORD record
ord-9c3a63c847d14f8381099385ce4af220
Source dataset
uspto-grants-1991_06
Patent number
US05021591

Reaction notes

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