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2-Acetylnaphthalene → HCID 51352711, compound

HRID 1406690
Notes
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Reaction equation

HRID 1406690 reaction equation
[C:1]([C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=1)(=[O:3])[CH3:2].[F:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[N:22]=[C:23]3[N:27]([C:28]=2[CH:29]=O)[CH:26]=[CH:25][S:24]3)=[CH:17][CH:16]=1.[OH-].[Na+]>C(O)C.C(OCC)(=O)C.CCCCCC>[F:14][C:15]1[CH:16]=[CH:17][C:18]([C:21]2[N:22]=[C:23]3[N:27]([C:28]=2/[CH:29]=[CH:2]/[C:1]([C:4]2[CH:13]=[CH:12][C:11]4[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=4)[CH:5]=2)=[O:3])[CH:26]=[CH:25][S:24]3)=[CH:19][CH:20]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 71222-AcetylnaphthaleneHCID 14798Sodium HydroxideHCID 27591026-(4-Fluorophenyl)imidazo[2,1-b][1,3]thiazole-5-carbaldehyde

Product 1

HCID 51352711HCID 51352711, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent
HCID 21226206
Ethyl acetate hexane
Solvent

Conditions

Temperature
27 °C

Procedure

To a stirred solution of 2-acetyl napthalene (170 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 (12e) as yellow solid (298 mg, 75% yield). Mp: 216-218° C.

Workup

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

Sources & evidence

ORD record
ord-80a3e0e1c9af4876bde65de86e5a53c2
Source dataset
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08916711B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes