Hydrochloric Acid → (2,4-Dimethoxy-benzylamino)-acetic acid

HRID 67306

反応式

HRID 67306 の反応式
NCC(O)=O.COC1C=C(OC)C=CC=1C=O.[OH-].[Na+].Cl.[CH3:21][O:22][C:23]1[CH:34]=[C:33]([O:35][CH3:36])[CH:32]=[CH:31][C:24]=1[CH2:25][NH:26][CH2:27][C:28]([OH:30])=[O:29].[Cl-].[Na+].[C:39]12[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=1)[NH:44][C:43](=[O:50])[O:42][C:40]2=O>CO.CS(C)=O.[Pd].O>[CH3:21][O:22][C:23]1[CH:34]=[C:33]([O:35][CH3:36])[CH:32]=[CH:31][C:24]=1[CH2:25][NH:26][CH2:27][C:28]([OH:30])=[O:29].[CH3:21][O:22][C:23]1[CH:34]=[C:33]([O:35][CH3:36])[CH:32]=[CH:31][C:24]=1[CH2:25][N:26]1[C:40](=[O:42])[C:39]2[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=2[NH:44][C:43](=[O:50])[CH2:27]1

参加物

13

反応物 7

HCID 313Hydrochloric AcidHCID 750GlycineHCID 5234Sodium ChlorideHCID 8359Isatoic AnhydrideHCID 14798Sodium HydroxideHCID 691752,4-DimethoxybenzaldehydeHCID 11042399(2,4-Dimethoxy-benzylamino)-acetic acid

生成物 2

HCID 11042399(2,4-Dimethoxy-benzylamino)-acetic acidHCID 217643143,4-dihydro-4-(2,4-dimethoxybenzyl)-2H-1,4-benzodiazepine-2,5(1H)-dione

試薬・触媒・溶媒 4

HCID 23938Palladium触媒HCID 679Dimethyl Sulfoxide溶媒HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

N-(2,4-dimethoxybenzyl)glycine is prepared by the reaction of glycine with 2,4-dimethoxybenzaldehyde in the presence of sodium hydroxide, reduction with palladium-on-carbon in methanol and subsequent neutralisation with 2 N hydrochloric acid. The aqueous solution obtained is concentrated. 41.9 g of this mixture of N-(2,4-dimethoxybenzyl)-glycine and sodium chloride are stirred at 110° C. for 1.5 hours in 300 ml of dimethyl sulphoxide with 23.18 g (142 mmol) of isatoic acid anhydride. The mixture is poured into ca 2 liters of water and stirred for 0.5 hour. The separated crystals are filtered off under suction, washed with water and dried. After recrystallisation from ethyl acetate, there is obtained 3,4-dihydro-4-(2,4-dimethoxybenzyl)-2H-1,4-benzodiazepine-2,5(1H)-dione of melting point 151°-152.5° C.

後処理

  1. customThe aqueous solution obtained
  2. concentrationis concentrated
  3. filtrationThe separated crystals are filtered off under suction
  4. washwashed with water
  5. customdried
  6. customAfter recrystallisation from ethyl acetate

出典と根拠

ORDレコード
ord-d465d0b9895e476187207aa393221ed8
出典データセット
uspto-grants-1982_08
特許番号
US04346030

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