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Trimethyl orthoformate → 2,2-Dimethyl-5-[({4-[3-(methyloxy)phenyl]-2-thienyl}amino)methylidene]-1,3-dioxane-4,6-dione

HRID 573565
Notes
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Reaction equation

HRID 573565 reaction equation
[CH3:1][C:2]1([CH3:10])[O:9][C:7](=[O:8])[CH2:6][C:4](=[O:5])[O:3]1.[CH:11](OC)(OC)OC.[CH3:18][O:19][C:20]1[CH:21]=[C:22]([C:26]2[CH:27]=[C:28]([NH2:31])[S:29][CH:30]=2)[CH:23]=[CH:24][CH:25]=1.C(=O)([O-])[O-].[K+].[K+]>>[CH3:1][C:2]1([CH3:10])[O:9][C:7](=[O:8])[C:6](=[CH:11][NH:31][C:28]2[S:29][CH:30]=[C:26]([C:22]3[CH:23]=[CH:24][CH:25]=[C:20]([O:19][CH3:18])[CH:21]=3)[CH:27]=2)[C:4](=[O:5])[O:3]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 4

HCID 9005Trimethyl orthoformateHCID 11430Potassium CarbonateHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 672362194-(3-Methoxyphenyl)thiophen-2-amine

Product 1

HCID 672359842,2-Dimethyl-5-[({4-[3-(methyloxy)phenyl]-2-thienyl}amino)methylidene]-1,3-dioxane-4,6-dioneYield 47.2%

Conditions

Temperature
110 °C

Procedure

Meldrum's acid (1.58 g, 10.96 mmol) was dissolved in trimethyl orthoformate (24.23 mL, 219 mmol) and the mixture was heated at 110° C. for 1 h. After cooling to RT, 4-[3-(methyloxy)phenyl]-2-thiophenamine (Description 40) (1.5 g, 7.31 mmol) was added to the mixture and reheated at 90° C. for 15 h. After cooling to RT, the mixture was evaporated in vacuo. The residue was dissolved in DCM and treated with potassium carbonate (3.03 g, 21.92 mmol). After stirring for 30 min, the mixture was filtered and the filtrate was evaporated in vacuo, to give the title compound (1.24 g). LCMS (A) m/z: 360 [M+1]+, Rt 1.19 min (acidic).

Workup

  1. temperatureAfter cooling to RT
  2. temperatureAfter cooling to RT
  3. customthe mixture was evaporated in vacuo
  4. dissolutionThe residue was dissolved in DCM
  5. filtrationthe mixture was filtered
  6. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-c1c37b9c54be475588cdb33f9232af08
Source dataset
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09029545B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes