Dimethylformamide → HCID 58625885, compound

HRID 131346Notes

Reaction equation

HRID 131346 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:14][C:13](=[S:15])[C:12]3[CH:11]=[C:10]([CH3:16])[S:9][C:8]=3[NH:7][C:6]=2[CH:17]=1.[CH3:18]N(C=O)C.C(=O)([O-])[O-].[K+].[K+].IC>O>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:14]=[C:13]([S:15][CH3:18])[C:12]3[CH:11]=[C:10]([CH3:16])[S:9][C:8]=3[NH:7][C:6]=2[CH:17]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 588606526-Fluoro-2-methyl-4,9-dihydro-3-thia-4,9-diazabenzo[f]azulene-10-thione

Product 1

HCID 58625885HCID 58625885, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Stir 6-fluoro-2-methyl-4,9-dihydro-3-thia-4,9-diaza-benzo[f]azulene-10-thione (61.5 g, 0.233 mol) and DMF (310 mL) under nitrogen for 15 minutes at ambient temperature. Add powdered potassium carbonate (67.7 g, 0.490 mol); stir 15 minutes at ambient temperature. Add iodomethane (22 mL, 0.35 mol); stir 4 hours at ambient temperature. Cool to 0-5° C. and add deionized water (150 mL) dropwise, keeping the temperature below 15° C. Extract the product with ethyl acetate. Wash the organic solution with brine four times, then dry over magnesium sulfate, filter and concentrate under reduced pressure to give 74.0 g of crude product. Purify by flash chromatography, eluting with 2:1/methylene chloride:heptane, then methylene chloride to give 55.0 g (85%) the title compound: 1H NMR (400 MHz, DMSO-d6) δ 8.11 (bs, 1H), 6.87 (m, 1H), 6.73 (m, 1H), 6.50 (s, 1H), 6.44 (m, 1H), 2.41(s, 3H), 2.25 (s, 3H). HRMS (ES) exact mass M+H calcd for C13H11FN2S2 279.0426; found 279.0416.

Workup

  1. stirringstir 4 hours at ambient temperature
  2. temperatureCool to 0-5° C.
  3. customthe temperature below 15° C
  4. extractionExtract the product with ethyl acetate
  5. washWash the organic solution with brine four times
  6. dry with materialdry over magnesium sulfate
  7. filtrationfilter
  8. concentrationconcentrate under reduced pressure
  9. customto give 74.0 g of crude product
  10. customPurify by flash chromatography
  11. washeluting with 2:1/methylene chloride

Sources & evidence

ORD record
ord-b040b18362ec430f9246e90efcc2e3ae
Source dataset
uspto-grants-2008_06
Patent number
US07384934B2

Reaction notes

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