Methyl iodide → HCID 57428829, compound

HRID 2267328Notes

Reaction equation

HRID 2267328 reaction equation
CN(C)/[CH:3]=[CH:4]/[C:5]([C:7]1[S:11][C:10]([C:12]([O:14]C)=[O:13])=[CH:9][CH:8]=1)=O.[NH2:17][C:18]([NH2:20])=[S:19].[CH3:21]C(C)([O-])C.[K+].C1COCC1.IC>COC(O)C>[CH3:21][S:19][C:18]1[N:20]=[C:5]([C:7]2[S:11][C:10]([C:12]([OH:14])=[O:13])=[CH:9][CH:8]=2)[CH:4]=[CH:3][N:17]=1

Participants

7

Reactant 5

HCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 2723790ThioureaHCID 23665647Potassium tert-butoxideHCID 57451715HCID 57451715, compound

Product 1

HCID 57428829HCID 57428829, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 30156371-MethoxyethanolSolvent

Procedure

A mixture of (E)-methyl 5-(3-(dimethylamino)acryloyl)thiophene-2-carboxylate (1.2 g, 5.02 mmol) and thiourea (0.38 g, 5.02 mmol) in methoxyethanol (20 mL) was treated slowly with 1.0 M potassium tert-butoxide in THF (5 mL, 5.02 mmol) at rt. The resulting mixture refluxed for 6 h. After cooling to rt, iodomethane (1.4 g, 10.04 mmol) was added and the mixture was stirred at rt for 15 h. The solvent was removed under vacuum and water (150 mL) was added to the residue. The mixture was extracted with ethyl acetate (3×100 mL). The combined organic layer was washed with brine (100 mL), dried over anhydrous sodium sulfate and filtered. The solvent was evaporated in vacuo and the solid was treated with methanol (10 mL) and filtered. The solid was suspended in 2.5 M sodium hydroxide (100 mL), stirred at rt for 24 h and extracted with ethyl acetate (50 mL). The aqueous layer was acidified with hydrochloric acid (6 N) and acetic acid to pH 5 and then extracted with ethyl acetate (3×70 mL). The combined organic layer was washed with brine (100 mL), dried over anhydrous sodium sulfate and filtered. The solvent was removed in vacuo and the solid treated with methanol (10 mL) and filtered to give the title compound (0.58 g, 48%). MS (M+H)+ 253.

Workup

  1. temperatureThe resulting mixture refluxed for 6 h
  2. customThe solvent was removed under vacuum and water (150 mL)
  3. additionwas added to the residue
  4. extractionThe mixture was extracted with ethyl acetate (3×100 mL)
  5. washThe combined organic layer was washed with brine (100 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customThe solvent was evaporated in vacuo
  9. additionthe solid was treated with methanol (10 mL)
  10. filtrationfiltered
  11. stirringstirred at rt for 24 h
  12. extractionextracted with ethyl acetate (50 mL)
  13. extractionextracted with ethyl acetate (3×70 mL)
  14. washThe combined organic layer was washed with brine (100 mL)
  15. dry with materialdried over anhydrous sodium sulfate
  16. filtrationfiltered
  17. customThe solvent was removed in vacuo
  18. additionthe solid treated with methanol (10 mL)
  19. filtrationfiltered

Sources & evidence

ORD record
ord-b832fb3691904ba386f2c38f56fb22f0
Source dataset
uspto-grants-2010_12
Patent number
US07858785B2

Reaction notes

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