Dimethylformamide → 7-Chloro-2-methyl-10-methylsulfanyl-4H-3-thia-4,9-diaza-benzo[f]azulene

HRID 131386ノート

反応式

HRID 131386 の反応式
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]2[NH:6][C:7]3[S:8][C:9]([CH3:15])=[CH:10][C:11]=3[C:12](=[S:14])[NH:13][C:4]=2[CH:3]=1.[CH3:18]N(C=O)C.C(=O)([O-])[O-].[K+].[K+].IC>CC(OC)(C)C>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]2[NH:6][C:7]3[S:8][C:9]([CH3:15])=[CH:10][C:11]=3[C:12]([S:14][CH3:18])=[N:13][C:4]=2[CH:3]=1

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 597321217-Chloro-2-methyl-4,9-dihydro-3-thia-4,9-diaza-benzo[f]azulene-10-thione

生成物 1

HCID 1360903747-Chloro-2-methyl-10-methylsulfanyl-4H-3-thia-4,9-diaza-benzo[f]azulene収率 96.7%

試薬・触媒・溶媒 1

HCID 15413tert-Butyl methyl ether溶媒

実験手順

Stir 7-chloro-2-methyl-4,9-dihydro-3-thia-4,9-diaza-benzo[f]azulene-10-thione (59.1 g, 0.210 mol) and DMF (236.4 mL) under nitrogen for 15 minutes at ambient temperature. Add powdered potassium carbonate (61.1 g, 0.442 mol); stir 15 minutes at ambient temperature. Add iodomethane (26.2 mL, 0.421 mol) and stir 2.5 hours at ambient temperature. Add MTBE (591 mL) and stir 15 minutes at ambient temperature. Filter and rinse solids with MTBE (59.1 mL). Wash the organic filtrate with water (3×591 mL), then dry over sodium sulfate, filter and concentrate under reduced pressure to give 60.0 g (96.7%) of crude product. 1H NMR (500 MHz, DMSO-d6) δ 2.22 (s, 3H), 2.39 (s, 3H), 6.47 (d, 1H), 6.57 (d, 1H), 6.86 (d, 1H), 6.97(dd, 1H), 8.09 (bs, 1H). 13C NMR (100 MHz, DMSO-d6) δ 13.24, 14.70, 120.58, 120.62, 121.67, 125.64, 127.51, 127.52, 127.77, 141.65, 142.16, 153.99, 165.48.

後処理

  1. filtrationFilter
  2. washrinse solids with MTBE (59.1 mL)
  3. washWash the organic filtrate with water (3×591 mL)
  4. dry with materialdry over sodium sulfate
  5. filtrationfilter
  6. concentrationconcentrate under reduced pressure

出典と根拠

ORDレコード
ord-164f807d1e4a49b1a9f3100890ce353b
出典データセット
uspto-grants-2008_06
特許番号
US07384934B2

反応ノート

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