反応式
[F:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([NH:9][C:10]2[S:11][C:12]([CH3:17])=[CH:13][C:14]=2[C:15]#[N:16])=[C:4]([N+:18]([O-])=O)[CH:3]=1.O.O.[Sn](Cl)[Cl:24].Cl>C(O)C>[ClH:24].[F:8][C:7]1[C:2]([F:1])=[CH:3][C:4]2[N:18]=[C:15]([NH2:16])[C:14]3[CH:13]=[C:12]([CH3:17])[S:11][C:10]=3[NH:9][C:5]=2[CH:6]=1参加物
5
反応条件
- 温度
- 86.5 °C
実験手順
Add 2-(4,5-difluoro-2-nitro-phenylamino)-5-methyl-thiophene-3-carbonitrile (94.0 g, 318 mmol) and tin (II) chloride dihydrate (225 g, 997 mmol) to ethanol (1400 mL) and aqueous 6N HCl (1400 mL) with stirring under nitrogen. Heat at gentle reflux (86-87° C.) for 0.3 hours, and then allow cooling to ambient temperature. Filter, rinse with water (3×250 mL) and dry at 50-60° C. to give 95.7 g (100%) of the title compound. 1H NMR (400 MHz, DMSO-d6) δ 11.41 (bs, 1H), 9.84 (bs, 1H), 9.33 (bs, 1H), 8.93 (bs, 1H), 7.00 (m, 2H), 6.85 (s, 1H), 2.28 (s, 3H). HRMS (ES) exact mass M+H calcd for C12H9F2N3S (freebase) 266.0563; found 266.0555.
後処理
- temperatureHeat
- temperatureallow cooling to ambient temperature
- filtrationFilter
- washrinse with water (3×250 mL)
- customdry at 50-60° C.
出典と根拠
- ORDレコード
- ord-864a9ab7a1f9408f9ff352b9bb18353c
- 出典データセット
- uspto-grants-2008_06
- 特許番号
- US07384934B2
関連ノート
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