Sodium Hydroxide → HCID 51352523, compound

HRID 1406687Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][C:12](C2C=CC=CC=2)=O)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[F:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[N:28]=[C:29]3[N:33]([C:34]=2[CH:35]=O)[CH:32]=[CH:31][S:30]3)=[CH:23][CH:22]=1.[OH-:37].[Na+]>C(O)C.C(OCC)(=O)C.CCCCCC>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11](=[O:37])/[CH:12]=[CH:35]/[C:34]2[N:33]3[C:29]([S:30][CH:31]=[CH:32]3)=[N:28][C:27]=2[C:24]2[CH:23]=[CH:22][C:21]([F:20])=[CH:26][CH:25]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

Conditions

Temperature: 27 °C

Procedure

To a stirred solution 3,4-dimethoxyphenyl acetophenone (180 mg, 2.7 mmol) and a 6-(4-fluorophenyl)imidazo[2,1-b]thiazol-5-carbaldehyde (246 mg, 2.7 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 columnchromatography using ethyl acetate:hexane (2:8) as a solvent system to obtain the pure product (8e) as yellow solid (306 mg, 75% yield). Mp: 221-223° 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 columnchromatography

Sources & evidence

ORD record: ord-33fbfb6d55c44791a90a7d7f4e95cdfc
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08916711B2

Reaction notes

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