Water → 10-hydroxymethylene-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one

HRID 1290743ノート

反応式

HRID 1290743 の反応式
CN([CH:4]=[C:5]1[C:17]2[N:16]3[CH:18]=[CH:19][N:20]=[C:15]3[C:14](=[O:21])[NH:13][C:12]=2[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]1=2)C.O.C(=O)([O-])[OH:24].[Na+]>Cl.CS(C)=O>[OH:24][CH:4]=[C:5]1[C:17]2[N:16]3[CH:18]=[CH:19][N:20]=[C:15]3[C:14](=[O:21])[NH:13][C:12]=2[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]1=2

参加物

6

反応物 3

HCID 962Water2 回HCID 516892Sodium BicarbonateHCID 5714456510-dimethylaminomethylene-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one

生成物 1

HCID 5702351210-hydroxymethylene-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 679Dimethyl Sulfoxide溶媒

実験手順

A solution of 1.4 g of 10-dimethylaminomethylene-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one in 35 ml of 5N hydrochloric acid is stirred for 30 minutes at a temperature in the region of 25° C. After addition of 60 ml of distilled water and neutralization with 120 ml of saturated aqueous sodium hydrogen carbonate solution, the solid formed is separated out by filtration, washed twice with 60 ml in total of distilled water and air-dried. The product obtained (1.1 g) is dissolved in 120 ml of dimethyl sulphoxide and, after addition of 120 ml of distilled water, the solid formed is separated out by filtration, washed twice with 10 ml in total of distilled water and twice with 10 ml in total of acetone and then dried under reduced pressure (1 mmHg; 0.13 kPa) at 100° C. 1 g of 10-hydroxymethylene-5H,10H-imidazo[1,2-a]indeno-[1,2-e]pyrazin-4-one is thus obtained as a 60/40 mixture of the Z and E forms, decomposing without melting at 290° C. [N.M.R. spectrum: (200 MHz; DMSO d6 ; δ in ppm): a 60/40 mixture of isomers is observed: from 7.20 to 7.40 (mt, 2H: --H7 and --H8); 7.56 and 7.64-8.29 and 8.79 (4s broad, twice 1H: --H of the imidazole); from 7.80 to 8.15 (mt, 2H: --H6 and --H9); 8.21 and 8.24 (2s, 1H in total: =CH--O--); 12.43 (cplx, 1H: --NH--)].

後処理

  1. customthe solid formed
  2. customis separated out by filtration
  3. washwashed twice with 60 ml in total of distilled water
  4. customair-dried
  5. customThe product obtained (1.1 g)
  6. customthe solid formed
  7. customis separated out by filtration
  8. washwashed twice with 10 ml in total of distilled water and twice with 10 ml in total of acetone
  9. customdried under reduced pressure (1 mmHg; 0.13 kPa) at 100° C

出典と根拠

ORDレコード
ord-0e46f6c6b3d34a70938b437abd7ae8ca
出典データセット
uspto-grants-1998_05
特許番号
US05753657

反応ノート

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