Butanal → HCID 57015719, compound

HRID 357079Notes

Reaction equation

[N:1]1[CH:2]=[CH:3][N:4]2[C:9]=1[CH:8]=[CH:7][N:6]=[C:5]2[S:10][CH2:11][CH2:12][CH2:13][CH2:14][N:15]1[C:19](=[O:20])[CH2:18][S:17][C:16]1=[O:21].N1C[CH2:26][CH2:25][CH2:24][CH2:23]1.C(=O)CCC>C(O)C>[CH:23](=[C:18]1[S:17][C:16](=[O:21])[N:15]([CH2:14][CH2:13][CH2:12][CH2:11][S:10][C:5]2[N:4]3[CH:3]=[CH:2][N:1]=[C:9]3[CH:8]=[CH:7][N:6]=2)[C:19]1=[O:20])[CH2:24][CH2:25][CH3:26]

Participants

Conditions

Temperature: 60 °C

Procedure

1.612 g (5 mmol) of 3-[4-(imidazo[1,2-c]pyrimidin-5-ylthio)butyl]thiazolidine-2,4-dione and 20 ml of ethanol were placed in a reaction flask, followed by stirring at 60° C. for 20 minutes, to dissolve the starting materials. After this mixture was kept standing to 50° C., an ethanol solution of 0.05 ml (0.5 mmol) of piperidine was added. Next, an ethanol solution of 0.45 ml (5 mmol) of n-butyraldehyde was added, followed by refluxing for 100 minutes. After the reaction mixture was cooled, the solvent was distilled off, followed by extraction with dichloromethane and water. After the organic layer was dried with sodium sulfate, the solvent was distilled off. The residue was eluted by column chromatography (eluent, hexane/ethyl acetate=1/4) to yield 1.052 g (55.9%, white crystal) of the desired product.

Workup

dissolutionto dissolve the starting materials
customwas kept standing to 50° C.
temperatureby refluxing for 100 minutes
temperatureAfter the reaction mixture was cooled
distillationthe solvent was distilled off
extractionfollowed by extraction with dichloromethane and water
dry with materialAfter the organic layer was dried with sodium sulfate
distillationthe solvent was distilled off
washThe residue was eluted by column chromatography (eluent, hexane/ethyl acetate=1/4)

Sources & evidence

ORD record: ord-9ec454b0f4144ffb850342d1389c2f69
Source dataset: uspto-grants-1998_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05840732

Reaction notes

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