1H-imidazole-2-carbaldehyde → HCID 12493308、化合物

HRID 2419641

反応式

HRID 2419641 の反応式
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]

参加物

8

反応物 5

HCID 249551H-imidazole-2-carbaldehyde2 回HCID 779181-BenzylimidazoleHCID 5668301H-Imidazole-2-methanol2 回HCID 3034069MethyldithiocarbazateHCID 137195915HCID 137195915、化合物

生成物 1

HCID 12493308HCID 12493308、化合物

試薬・触媒・溶媒 2

HCID 176Acetic Acid触媒HCID 702Ethanol溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-5f9a779535df4c16897b7a1c151c7769
出典データセット
uspto-grants-1978_08
特許番号
US04107309

関連ノート

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