Ethyl Acetate → Methyl 6-chloro-5-isothiocyanatonicotinate

HRID 1426162

반응식

HRID 1426162 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

HCID 86639699Methyl 6-chloro-5-isothiocyanatonicotinate수율 76.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-0a7ff6a18d04445fb83ada702e8df418
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08933077B2

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