Hydrochloric Acid → 6-chloro-3-[(4-hydroxyphenyl)thio]-N-(3-methyl-1,2,4-thiadiazol-5-yl)pyridine-2-carboxamide

HRID 2196603노트

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HRID 2196603 반응식
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[C:16]1[C:17]([C:23]([NH:25][C:26]2[S:30][N:29]=[C:28]([CH3:31])[N:27]=2)=[O:24])=[N:18][C:19]([Cl:22])=[CH:20][CH:21]=1.Cl>O.C(Cl)(Cl)Cl.CN(C)C=O>[Cl:22][C:19]1[N:18]=[C:17]([C:23]([NH:25][C:26]2[S:30][N:29]=[C:28]([CH3:31])[N:27]=2)=[O:24])[C:16]([S:8][C:5]2[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][CH:4]=2)=[CH:21][CH:20]=1

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 2401474-MercaptophenolHCID 866196083,6-dichloro-N-(3-methyl-1,2,4-thiadiazol-5-yl)pyridine-2-carboxamide

생성물 1

HCID 866196096-chloro-3-[(4-hydroxyphenyl)thio]-N-(3-methyl-1,2,4-thiadiazol-5-yl)pyridine-2-carboxamide수율 71.7%

시약·촉매·용매 3

HCID 962Water용매HCID 6212Chloroform용매HCID 6228Dimethylformamide용매

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온도
50 °C

실험 절차

12 g of 4-hydroxythiophenol and 16 g of potassium carbonate were added to a dimethylformamide (150 ml) solution of 15 g of 3,6-dichloro-N-(3-methyl-1,2,4-thiadiazol-5-yl)pyridine-2-carboxamide, and stirred at 50° C. for 1.5 hours. At room temperature, chloroform and water were added to it, and its pH was controlled to 3 with aqueous 2 N hydrochloric acid solution added thereto. This was extracted with chloroform, the organic layer was washed with saturated saline water, and dried with anhydrous magnesium sulfate. The solvent was evaporated away under reduced pressure, 300 ml of t-butyl methyl ether was added to the residue, and the resulting solid was taken out through filtration to obtain 14.1 g of the entitled compound as a yellow solid.

후처리

  1. additionadded
  2. extractionThis was extracted with chloroform
  3. washthe organic layer was washed with saturated saline water
  4. dry with materialdried with anhydrous magnesium sulfate
  5. customThe solvent was evaporated away under reduced pressure, 300 ml of t-butyl methyl ether
  6. additionwas added to the residue
  7. filtrationthe resulting solid was taken out through filtration

출처 및 근거

ORD 기록
ord-9a0d1f3899ad495b9fbb8ede46593eef
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08338460B2

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