Ethyl Acetate → Methyl 6-chloro-5-isothiocyanatonicotinate

HRID 1426162

反応式

HRID 1426162 の反応式
[C:1](Cl)(Cl)=[S:2].[NH2:5][C:6]1[C:7]([Cl:16])=[N:8][CH:9]=[C:10]([CH:15]=1)[C:11]([O:13][CH3:14])=[O:12].C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C>ClCCl>[Cl:16][C:7]1[C:6]([N:5]=[C:1]=[S:2])=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][N:8]=1

参加物

6

反応物 4

HCID 8857Ethyl AcetateHCID 10040ThiophosgeneHCID 10340Sodium CarbonateHCID 18412438Methyl 5-amino-6-chloropyridine-3-carboxylate

生成物 1

HCID 86639699Methyl 6-chloro-5-isothiocyanatonicotinate収率 76.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

Thiophosgene (6.367 g, 55.37 mmol) in dichloromethane (10 mL) was added to a mixture of methyl 5-amino-6-chloronicotinate (8.61 g, 46.14 mmol) and sodium carbonate (9.781 g, 92.29 mmol) in dichloromethane (200 mL). The reaction mixture was stirred for four days at ambient temperature. The reaction mixture was washed with water and brine, dried, and concentrated. The residue was purified via MPLC (Biotage) eluting with 12:1 hexane:ethyl acetate to afford methyl 6-chloro-5-isothiocyanatonicotinate (8.03 g, 76.1% yield) as a white solid: 1H NMR (CDCl3) δ 3.97 (s, 3H), 8.09 (s, 1H), 8.84 (s, 1H).

後処理

  1. washThe reaction mixture was washed with water and brine
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was purified via MPLC (Biotage)
  5. washeluting with 12:1 hexane

出典と根拠

ORDレコード
ord-0a7ff6a18d04445fb83ada702e8df418
出典データセット
uspto-grants-2015_01
特許番号
US08933077B2

関連ノート

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