Sodium Hydroxide → HCID 68360759, compound

HRID 1406689Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10](C2C=CC=CC=2)=O)[CH:5]=[CH:6][C:7]=1[CH3:8].[F:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[N:26]=[C:27]3[N:31]([C:32]=2[CH:33]=O)[CH:30]=[CH:29][S:28]3)=[CH:21][CH:20]=1.[OH-:35].[Na+]>C(O)C.C(OCC)(=O)C.CCCCCC>[CH3:1][C:2]1[CH:3]=[C:4]([C:9](=[O:35])/[CH:10]=[CH:33]/[C:32]2[N:31]3[C:27]([S:28][CH:29]=[CH:30]3)=[N:26][C:25]=2[C:22]2[CH:21]=[CH:20][C:19]([F:18])=[CH:24][CH:23]=2)[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

Conditions

Temperature: 27 °C

Procedure

To a stirred solution of 3,4-dimethylphenyl acetophenone (148 mg, 1.0 mmol) and a 6-(4-fluorophenyl)imidazo[2,1-b]thiazol-5-carbaldehyde (246 mg, 1.0 mmol) in ethanol (20 ml) 10% aqueous solution of NaOH was added (5 ml). The reaction mixture was stirred at room temperature 27° C. for 4 h and the reaction was monitored by TLC using ethyl acetate-hexane (3:7) as a solvent system. The solvent was evaporated under vacuum then the residue was dissolved in ethylacetate/water. The organic layer was washed with brine and evaporated. This was further purified by column chromatography using ethyl acetate:hexane (2:8) as a solvent system to obtain the pure product (9e) as yellow solid (286 mg, 76% yield). Mp: 210-213° C.

Workup

customThe solvent was evaporated under vacuum
dissolutionthe residue was dissolved in ethylacetate/water
washThe organic layer was washed with brine
customevaporated
customThis was further purified by column chromatography

Sources & evidence

ORD record: ord-521e1d5e42eb408089e33c3801b50edc
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08916711B2

Reaction notes

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