Stannous chloride dihydrate → 2-tert-Butyl-4H-3-thia-4,9-diaza-benzo[f]azulen-10-ylamine hydrochloride

HRID 131375ノート

反応式

HRID 131375 の反応式
[C:1]([C:5]1[S:9][C:8]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N+:17]([O-])=O)=[C:7]([C:20]#[N:21])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].O.O.[Sn](Cl)[Cl:25]>Cl.C(O)C>[ClH:25].[C:1]([C:5]1[S:9][C:8]2[NH:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:17]=[C:20]([NH2:21])[C:7]=2[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

参加物

5

反応物 2

HCID 61436Stannous chloride dihydrateHCID 210935385-tert-Butyl-2-(2-nitro-phenylamino)-thiophene-3-carbonitrile

生成物 1

HCID 1357977472-tert-Butyl-4H-3-thia-4,9-diaza-benzo[f]azulen-10-ylamine hydrochloride収率 90%

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 702Ethanol溶媒

実験手順

Add 5-tert-butyl-2-(2-nitro-phenylamino)-thiophene-3-carbonitrile (21.2 g, 70 mmol) to a solution of tin(II)chloride dihydrate (46.1 g, 209 mmol) in conc. HCl (200 mL) and ethanol (600 mL). Reflux the mixture for 2 hours. Concentrate the solution to 200 mL and add to water (1 L). Filter and wash with water then hexanes to obtain the title compound as an orange powder (19.4 g): 1H NMR (DMSO-d6) δ 1.27 (s, 9H), 6.86 (d, 1H), 6.89 (s, 1H), 6.95 (d, 1H), 7.03 (t, 1H), 7.11 (t, 1H), 8.69 (s, 1H), 9.11 (s, 1H), 9.52 (s, 1H), 10.88 (s, 1H); MS (APCI) m/z (rel intensity) 272 (100).

後処理

  1. temperatureReflux the mixture for 2 hours
  2. concentrationConcentrate the solution to 200 mL
  3. additionadd to water (1 L)
  4. filtrationFilter
  5. washwash with water

出典と根拠

ORDレコード
ord-e7944825a9da4c3ab6013f61ff6e1ea5
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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