Triethylamine → 5,6-difluorobenzo[c][1,2,5]thiadiazole

HRID 335357ノート

反応式

HRID 335357 の反応式
[F:1][C:2]1[CH:3]=[C:4]([NH2:10])[C:5]([NH2:9])=[CH:6][C:7]=1[F:8].C(N(CC)CC)C.O=[S:19](Cl)Cl>ClCCl>[F:1][C:2]1[C:7]([F:8])=[CH:6][C:5]2[C:4]([CH:3]=1)=[N:10][S:19][N:9]=2

参加物

5

反応物 3

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 27367551,2-Diamino-4,5-difluorobenzene

生成物 1

HCID 665541575,6-difluorobenzo[c][1,2,5]thiadiazole収率 58.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 4,5-difluorobenzene-1,2-diamine (2.0 g, 0.014 mol) and triethylamine (7.8 mL, 0.056 mol) in dichloromethane (80 mL) was added SOCl2 (4.04 mL, 0.055 mol) dropwise at room temperature. The resulting reaction mixture was heated to reflux overnight. The reaction mixture was then allowed to cool to room temperature, and quenched with water carefully. The resulting mixture was extracted with dichloromethane, dried over Na2SO4 and concentrated on a rotary evaporator to give a white solid as the crude compound. The crude product was purified by flash column chromatography (silica gel, hexanes) to afford 5,6-difluorobenzo[1,2,5]thiadiazole as a white crystalline solid (1.4 g, 58% yield). 1H NMR (CDCl3 500 MHz): δ: 7.76 (t, 2H, J=8.5 Hz). 13C NMR (CDCl3, 500 MHz): δ 154.94, 154.78, 152.86, 152.70, 150.89, 150.85, 150.81, 106.26, 106.21, 106.14, 106.09. Anal. calcd. for (C6H2F2N2S): C, 41.86; H, 1.17; N, 16.27. Found: C, 41.41; H, 1.22; H, 15.87. m.p: 64-65° C.

後処理

  1. customThe resulting reaction mixture
  2. temperaturewas heated
  3. temperatureto reflux overnight
  4. customquenched with water carefully
  5. extractionThe resulting mixture was extracted with dichloromethane
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated on a rotary evaporator
  8. customto give a white solid as the crude compound
  9. customThe crude product was purified by flash column chromatography (silica gel, hexanes)

出典と根拠

ORDレコード
ord-3b57aeca8a3f4eccbab87d1848b9bd9a
出典データセット
uspto-grants-2014_11
特許番号
US08883958B2

反応ノート

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