Sodium Hydroxide → HCID 54613685, compound

HRID 1406688Notes

Reaction equation

[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH2:10][C:11](C3C=CC=CC=3)=O)=[CH:4][C:3]=2[O:2]1.[CH3:19][O: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>[O:9]1[C:8]2[CH:7]=[CH:6][C:5]([C:10](=[O:37])/[CH:11]=[CH:35]/[C:34]3[N:33]4[C:29]([S:30][CH:31]=[CH:32]4)=[N:28][C:27]=3[C:24]3[CH:23]=[CH:22][C:21]([O:20][CH3:19])=[CH:26][CH:25]=3)=[CH:4][C:3]=2[O:2][CH2:1]1

Participants

Conditions

Temperature: 27 °C

Procedure

To a stirred solution 3,4-methylenedioxy phenyl acetophenone (164 mg, 1.0 mmol) and a 6-(4-methoxyphenyl)imidazo[2,1-b]thiazol-5-carbaldehyde (258 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 (11a) as yellow solid (323 mg, 80% yield). Mp: 189-191° 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-7d5bd9e07b9e41fa976e6e62d4fbf64c
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08916711B2

Reaction notes

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