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Chloroacetyl chloride → HCID 22350167、化合物

HRID 900807
ノート
印刷プレビュー

反応式

HRID 900807 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[OH:11])[NH:7][C:6]([C:12]([O:14][CH3:15])=[O:13])=[CH:5]2.[O:16]1CC[CH2:18][CH2:17]1.C(=O)([O-])O.[Na+].ClCC(Cl)=O.C(=O)([O-])[O-].[K+].[K+]>>[O:16]=[C:17]1[CH2:18][O:11][C:10]2[CH:9]=[C:8]3[NH:7][C:6]([C:12]([O:14][CH3:15])=[O:13])=[CH:5][C:4]3=[CH:3][C:2]=2[NH:1]1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 5

HCID 6577Chloroacetyl chlorideHCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 22350178Methyl 5-amino-6-hydroxy-indole-2-carboxylate

生成物 1

HCID 22350167HCID 22350167、化合物収率 71.2%

実験手順

To a solution of 2.0 g (9.7 mmol) of methyl 5-amino-6-hydroxy-indole-2-carboxylate (Example 5/c) in 300 ml of tetrahydrofuran 2.45 g (29.2 mmol) of sodium hydrogencarbonate and 1.3 ml (16.3 mmol) of chloroacetyl chloride are added and the mixture is stirred at room temperature overnight. The reaction mixture is concentrated and 100 ml of water is added to the residue. The precipitated crystals are filtered off, washed with water and suspended in 120 ml of acetonitrile. 4.05 g (29.3 mmol) of potassium carbonate is added to the suspension and the resulted mixture is stirred at room temperature overnight. The reaction mixture is concentrated and 100 ml of water is added to the residue. The product is filtered off, washed with water and dried to yield 1.7 g (71%) of the title compound. Mp.: 188-196° C. (water).

後処理

  1. concentrationThe reaction mixture is concentrated
  2. addition100 ml of water is added to the residue
  3. filtrationThe precipitated crystals are filtered off
  4. washwashed with water
  5. stirringthe resulted mixture is stirred at room temperature overnight
  6. concentrationThe reaction mixture is concentrated
  7. addition100 ml of water is added to the residue
  8. filtrationThe product is filtered off
  9. washwashed with water
  10. customdried

出典と根拠

ORDレコード
ord-ec5f0de937ff4957816dc83ae51cb349
出典データセット
uspto-grants-2008_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07361670B2

反応ノート

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