Methyl formate → Sodium 3-cyano-6-oxo-1-phenyl-1,6-dihydropyridine-2-thiolate

HRID 1455522노트

반응식

HRID 1455522 반응식
[CH3:1][O-].[Na+:3].CCO[C:7]([CH3:9])=[O:8].C(OC)=O.[C:14]([CH2:16][C:17]([NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[S:18])#[N:15]>CO.CCO>[C:14]([C:16]1[CH:1]=[CH:9][C:7](=[O:8])[N:19]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:17]=1[S-:18])#[N:15].[Na+:3]

참가 물질

7

반응물 4

HCID 7865Methyl formateHCID 8857Ethyl AcetateHCID 27713122-cyano-N-phenylethanethioamideHCID 10942334Sodium Methoxide2회

생성물 1

HCID 11615758Sodium 3-cyano-6-oxo-1-phenyl-1,6-dihydropyridine-2-thiolate수율 100%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 887Methanol용매

실험 절차

Sodium methoxide (2.88 g) was added to EtOAc (8.7 mL), cooled to +14° C. To the resulting suspension was added methyl formate (2.2 mL) slowly over 4.3 h whilst maintaining the reaction temperature at +14° C. After this time, the temperature was adjusted to +25° C. and the reaction was allowed to stir out at this temperature overnight. Absolute EtOH (25 mL) and a solution of sodium methoxide in MeOH (30 wt %, 6.7 mL) were then added followed by 2-cyano-N-phenylthioacetamide (5 g) and the resulting mixture was heated at reflux for 24 h. The reaction was cooled to +5° C. when the product was recovered by filtration. The filter cake was washed with cold (+5° C.) absolute EtOH (20 ml) and then dried to constant weight under vacuum at 45° C. to give the title compound as a pale pink solid (2.77 g; equivalent to 2.63 g at 100%). δH (DMSO-d6) 7.32 (2H, m), 7.27-7.18 (1H, m), 7.16 (1H, d, J 9.1 Hz), 6.92 (2H, m), 5.63 (1H, d, J 9.1 Hz). LCMS (ES+) RT 2.43 minutes, 229 (M+H)+.

후처리

  1. temperaturecooled to +14° C
  2. temperaturewhilst maintaining the reaction temperature at +14° C
  3. customwas adjusted to +25° C.
  4. temperaturethe resulting mixture was heated
  5. temperatureat reflux for 24 h
  6. temperatureThe reaction was cooled to +5° C. when the product
  7. filtrationwas recovered by filtration
  8. washThe filter cake was washed with cold (+5° C.) absolute EtOH (20 ml)
  9. customdried to constant weight under vacuum at 45° C.

출처 및 근거

ORD 기록
ord-85d9d138714e4a1b9983f6a38abd9cbb
출처 데이터셋
uspto-grants-2009_01
특허 번호
US07482452B2

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