1H-imidazole-2-carbaldehyde → HCID 12493308, 화합물

HRID 2419641

반응식

HRID 2419641 반응식
C(N1C=CN=C1)C1C=CC=CC=1.OCC1NC=CN=1.N1C=CN=C1C=O.C(SC)(=S)NN.[NH:33]1[CH:37]=[CH:36][N:35]=[C:34]1[CH:38]=[N:39][NH:40][C:41]([S:43]C)=S>C(O)(=O)C.C(O)C>[N:33]1[CH:37]=[CH:36][N:35]2[C:34]=1[CH:38]=[N:39][NH:40][C:41]2=[S:43]

참가 물질

8

반응물 5

HCID 249551H-imidazole-2-carbaldehyde2회HCID 779181-BenzylimidazoleHCID 5668301H-Imidazole-2-methanol2회HCID 3034069MethyldithiocarbazateHCID 137195915HCID 137195915, 화합물

생성물 1

HCID 12493308HCID 12493308, 화합물

시약·촉매·용매 2

HCID 176Acetic Acid촉매HCID 702Ethanol용매2회

실험 절차

N-Benzylimidazole is converted to 2-hydroxymethylimidazole by the method of R. G. Jones, J.A.C.S. 71, 383 (1949). The 2-hydroxymethylimidazole is converted to imidazole-2-carboxaldehyde by the method of H. Schubert and H. D. Rudorf, Angew. Chem. Intern. Ed., 5, 674 (1966). A 67.) gm. portion of imidazole-2-carboxaldehyde is added to 500 ml. of ethanol and warmed on a steam bath. An 85.4 gm. portion of methyl dithiocarbazate is added together with 200 ml. of ethanol. While the solution is warm, 20 drops of glacial acetic acid are added. The mixture is heated to reflux on a steam bath for one hour, cooled and filtered. The filtrate is evaporated yielding 123.2 gm. of 3-(2-imidazolymethylene)-dithio-carbazic acid, methyl ester. A 120.2 g. portion of 3-(2-imidazolylmethylene)dithio-carbazic acid, methyl ester is added to 800 ml. of diphenyl ester. The mixture is heated in an oil bath at 195°-200° C. for 15 minutes. The reaction mixture is cooled to room temperature and the precipitate is collected, washed with petroleum ether, and air dried. This light orange solid is crystallized twice from petroleum ether giving 83.0 gm. of imidazo[1,2-d]-as-triazine-5(6H)-thione, m.p. 238°-240° C.

후처리

  1. temperatureWhile the solution is warm
  2. temperatureThe mixture is heated
  3. temperatureto reflux on a steam bath for one hour
  4. temperaturecooled
  5. filtrationfiltered
  6. customThe filtrate is evaporated
  7. customyielding 123.2 gm
  8. temperatureThe mixture is heated in an oil bath at 195°-200° C. for 15 minutes
  9. customthe precipitate is collected
  10. washwashed with petroleum ether, and air
  11. customdried
  12. customThis light orange solid is crystallized twice from petroleum ether giving 83.0 gm

출처 및 근거

ORD 기록
ord-5f9a779535df4c16897b7a1c151c7769
출처 데이터셋
uspto-grants-1978_08
특허 번호
US04107309

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