Acetic Acid → Urea, N-(6-chloro-5-(2-fluorophenyl)-2,3-dihydro-1-methyl-2-oxo-1H-1,4-benzodiazepin-7-yl)-N(sup 1)-(2-hydroxyethyl)-

HRID 1413788ノート

反応式

HRID 1413788 の反応式
C([O:4][CH2:5][CH2:6][NH:7][C:8]([NH:10][C:11]1[CH:12]=[CH:13][C:14]2[N:20]([CH3:21])[C:19](=[O:22])[CH2:18][N:17]=[C:16]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[F:29])[C:15]=2[C:30]=1[Cl:31])=[O:9])(=O)C.C[O-].[Na+].C(O)(=O)C>CO>[Cl:31][C:30]1[C:15]2[C:16]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[F:29])=[N:17][CH2:18][C:19](=[O:22])[N:20]([CH3:21])[C:14]=2[CH:13]=[CH:12][C:11]=1[NH:10][C:8]([NH:7][CH2:6][CH2:5][OH:4])=[O:9]

参加物

5

反応物 3

HCID 176Acetic AcidHCID 10942334Sodium MethoxideHCID 20562372HCID 20562372、化合物

生成物 1

HCID 3058274Urea, N-(6-chloro-5-(2-fluorophenyl)-2,3-dihydro-1-methyl-2-oxo-1H-1,4-benzodiazepin-7-yl)-N(sup 1)-(2-hydroxyethyl)-

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

600 mg of 2-[3-[6-chloro-5-(o-fluorophenyl)-2,3-dihydro-1-methyl-2-oxo-1H-1,4-benzodiazepin-7-yl]ureido]ethyl acetate dissolved in 35 ml of absolute methanol are treated with 830 mg of sodium methylate and stirred at room temperature for 1 hour. The mixture is buffered with a small amount of acetic acid and concentrated. The residue is treated with methylene chloride/10% sodium bicarbonate solution, the aqueous solution is extracted with methylene chloride and the organic solution is dried over sodium sulphate, filtered and concentrated. The residue is purified on a 30 g silica gel column with ethyl acetate/methanol (10:1) as the eluting agent and crystallised from ethanol/ether. There is obtained 1-[6-chloro-5-(o-fluorophenyl)-2,3-dihydro-1-methyl-2-oxo-1H-1,4-benzodiazepin-7-yl]-3-(2-hydroxyethyl)urea which, according to the melting point, mixed melting point and IR spectrum, is identical with a sample prepared in another manner (see Example 13).

後処理

  1. concentrationconcentrated
  2. additionThe residue is treated with methylene chloride/10% sodium bicarbonate solution
  3. extractionthe aqueous solution is extracted with methylene chloride
  4. dry with materialthe organic solution is dried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue is purified on a 30 g silica gel column with ethyl acetate/methanol (10:1) as the eluting agent
  8. customcrystallised from ethanol/ether

出典と根拠

ORDレコード
ord-ec97ca4ce31e464e9b40f1e88abaa2a1
出典データセット
uspto-grants-1981_02
特許番号
US04251443

反応ノート

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