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

HRID 67405

반응식

HRID 67405 반응식
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

참가 물질

13

반응물 7

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

생성물 2

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

시약·촉매·용매 4

HCID 23938Palladium촉매HCID 679Dimethyl Sulfoxide용매HCID 887Methanol용매HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-39334f19e71744d793e29b729d245f50
출처 데이터셋
uspto-grants-1982_08
특허 번호
US04346032

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