Ammonia → 4-Carbamoyl-5-(pyrazin-2-yl)-1,2-dithiole-3-thione

HRID 1390313노트

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HRID 1390313 반응식
[C:1]([C:4]1[C:5](=[S:15])[S:6][S:7][C:8]=1[C:9]1[CH:14]=[N:13][CH:12]=[CH:11][N:10]=1)(O)=[O:2].C(OC([N:21]1C2C(=CC=CC=2)C=CC1OCC)=O)C.N>C(Cl)Cl.CO.CN(C)C=O>[C:1]([C:4]1[C:5](=[S:15])[S:6][S:7][C:8]=1[C:9]1[CH:14]=[N:13][CH:12]=[CH:11][N:10]=1)(=[O:2])[NH2:21]

참가 물질

7

반응물 3

HCID 222AmmoniaHCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinolineHCID 213291664-Carboxy-5-(pyrazin-2-yl)-1,2-dithiole-3-thione

생성물 1

HCID 213291974-Carbamoyl-5-(pyrazin-2-yl)-1,2-dithiole-3-thione수율 51.6%

시약·촉매·용매 3

HCID 887Methanol용매HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

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온도
20 °C

실험 절차

A suspension of 4-carboxy-5-(pyrazin-2-yl)-1,2-dithiole-3-thione (12.8 g) [prepared as described in Example 32] and 1-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline (13.25 g) in methylene chloride (40 cc) is stirred for 5 hours at a temperature of about 20° C. A solution (15 cc) of 4N ammonia in methanol is added over a period of 10 minutes to the solution obtained, and the reaction mixture is stirred for a further 5 minutes at a temperature of about 20° C. The insoluble product is filtered off and washed successively with methylene chloride (50 cc), saturated aqueous sodium bicarbonate solution (25 cc), water (4 × 100 cc) and then ethyl acetate (15 cc). The residue obtained is dissolved at a temperature of about 100° C. in dimethylformamide (100 cc) and the solution, which is filtered hot, is then poured into distilled water (200 cc). After cooling to a temperature of about 20° C., the insoluble product is filtered off and washed with ethyl acetate (2 × 10 cc) to give 4-carbamoyl-5-(pyrazin-2-yl)-1,2-dithiole-3-thione (6.58 g) melting at 267° C.

후처리

  1. customobtained
  2. stirringthe reaction mixture is stirred for a further 5 minutes at a temperature of about 20° C
  3. filtrationThe insoluble product is filtered off
  4. washwashed successively with methylene chloride (50 cc), saturated aqueous sodium bicarbonate solution (25 cc), water (4 × 100 cc)
  5. customThe residue obtained
  6. filtrationthe solution, which is filtered hot
  7. additionis then poured
  8. distillationinto distilled water (200 cc)
  9. temperatureAfter cooling to a temperature of about 20° C.
  10. filtrationthe insoluble product is filtered off
  11. washwashed with ethyl acetate (2 × 10 cc)

출처 및 근거

ORD 기록
ord-90b756c3b6644ed6b4a3613d02bca067
출처 데이터셋
uspto-grants-1979_02
특허 번호
US04138487

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