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Acetic Acid → 10-acetamido-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one

HRID 1290740
ノート
印刷プレビュー

反応式

HRID 1290740 の反応式
O/[N:2]=[C:3]1\[C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:9]=2[C:10]2[NH:11][C:12](=[O:19])[C:13]3[N:14]([CH:16]=[CH:17][N:18]=3)[C:15]\1=2.C.[C:21](O)(=[O:23])[CH3:22]>O.CN(C)C=O.[Zn]>[C:21]([NH:2][CH:3]1[C:15]2[N:14]3[CH:16]=[CH:17][N:18]=[C:13]3[C:12](=[O:19])[NH:11][C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]1=2)(=[O:23])[CH3:22]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 176Acetic Acid2 回HCID 297MethaneHCID 178518651HCID 178518651、化合物

生成物 1

HCID 1529136110-acetamido-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one

試薬・触媒・溶媒 3

HCID 23994Zinc触媒HCID 962Water溶媒
HCID 6228
Dimethylformamide
溶媒

実験手順

A suspension of 5.25 g of 10-(E-hydroxy-imino)-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one and 2.9 g of zinc powder in 100 ml of acetic acid is heated for 2 hours at a temperature between 80° C. and 90° C. After addition of 100 ml of acetic acid, the mixture is filtered and the filtrate is concentrated to dryness under reduced pressure (10 mmHg; 2 kPa) at 65° C. The product obtained (3.8 g) is suspended in 100 ml of distilled water, filtered, washed with 10 ml of distilled water and with 10 ml of acetone and then dried under reduced pressure (15 mmHg; 2 kPa) at 20° C. The product obtained (2 g) is dissolved in 60 ml of boiling dimethylformamide and, after addition of 0.1 g of decolorizing charcoal, the solution is filtered while hot. The filter is washed with 10 ml of boiling dimethylformamide and the filtrate and the combined washings are then stored for 4 hours at a temperature in the region of 20° C. The crystals formed are separated out by filtration, washed successively with 10 ml of dimethylformamide, 10 ml of distilled water and 10 ml of acetone and dried to dryness under reduced pressure (1 mmHg; 0.13 kPa) at 100° C. 0.43 g of 10-acetamido-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one is thus obtained, decomposing without melting at 330° C. [N.M.R. spectrum: (200 MHz; DMSO d6 ; δ in ppm): 2.00 (s, 3H: --CO--CH3); 6.13 (d, J=8.5 Hz, 1H: CH--N); 7.35 and 7.48 (2t, J=7.5 Hz, 1H each: --H7 and --H8); 7.48 and 7.85 (2d, J=7.5 Hz, 1H each: --H6 and --H9); 7.58 and 7.65 (2s broad, 1H each: --H of the imidazole); 8.58 (d, J=8.5 Hz, 1H: --NH--COCH3); 12.50 (cplx, 1H: --NH--)].

後処理

  1. temperatureis heated for 2 hours at a temperature between 80° C. and 90° C
  2. filtrationthe mixture is filtered
  3. concentrationthe filtrate is concentrated to dryness under reduced pressure (10 mmHg; 2 kPa) at 65° C
  4. customThe product obtained (3.8 g)
  5. filtrationfiltered
  6. washwashed with 10 ml of distilled water and with 10 ml of acetone
  7. customdried under reduced pressure (15 mmHg; 2 kPa) at 20° C
  8. customThe product obtained (2 g)
  9. filtrationthe solution is filtered while hot
  10. washThe filter is washed with 10 ml of boiling dimethylformamide
  11. customThe crystals formed
  12. customare separated out by filtration
  13. washwashed successively with 10 ml of dimethylformamide, 10 ml of distilled water and 10 ml of acetone
  14. customdried to dryness under reduced pressure (1 mmHg; 0.13 kPa) at 100° C

出典と根拠

ORDレコード
ord-71bccbee2d824964be3b90f31bdfac64
出典データセット
uspto-grants-1998_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05753657

反応ノート

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