Benzaldehyde → 3-(2,1,3-Benzothiadiazol-5-yl)-5-hydroxy-5-(4-methoxyphenyl)-4-(phenylmethyl)-2(5H)-furanone

HRID 850637

반응식

HRID 850637 반응식
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:9]1[S:10][N:11]=[C:12]2[CH:17]=[C:16]([CH:18]([CH2:24][C:25]([C:27]3[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=3)=[O:26])[C:19]([O:21]CC)=[O:20])[CH:15]=[CH:14][C:13]=12.C(=O)([O-])[O-].[K+].[K+].S(=NC1C=CC=CC=1)=O.[Na]>CC(C)=O.C1(C)C=CC=CC=1.CO.C(O)(=O)C>[N:9]1[S:10][N:11]=[C:12]2[CH:17]=[C:16]([C:18]3[C:19](=[O:21])[O:20][C:25]([OH:26])([C:27]4[CH:28]=[CH:29][C:30]([O:33][CH3:34])=[CH:31][CH:32]=4)[C:24]=3[CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:15]=[CH:14][C:13]=12

참가 물질

10

반응물 5

HCID 240BenzaldehydeHCID 11430Potassium CarbonateHCID 70739Benzenamine, N-sulfinyl-HCID 5360545SodiumHCID 10926758Ethyl 2-(2,1,3-benzothiadiazol-5-yl)-4-(4-methoxyphenyl)-4-oxobutanoate

생성물 1

HCID 154104553-(2,1,3-Benzothiadiazol-5-yl)-5-hydroxy-5-(4-methoxyphenyl)-4-(phenylmethyl)-2(5H)-furanone

시약·촉매·용매 4

HCID 176Acetic Acid용매HCID 180Acetone용매HCID 887Methanol용매HCID 1140Toluene용매

실험 절차

0.38 g of benzaldehyde and 120 g of ethyl 2-(2,1,3-benzothiadiazol-5-yl)-4-(4-methoxyphenyl)-4-oxo-butanoate ("A"), m.p. 89°, (obtainable by reaction of 5.5 g of ethyl 2-(2,1,3-benzothiadiazol-5-yl) acetate with 5.5 g of 2'-bromo-4-methoxyacetophenone and 4 g of potassium carbonate in 200 ml of acetone, 18 hours under reflux; ethyl 2-(2,1,3-benzothiadiazol-5-yl) acetate, m.p. 40-41°, is obtained by reaction of 24.3 g of ethyl 3,4-diaminophenyl acetate and 26.9 ml of thionylaniline in 80 ml of toluene, 4 hours under reflux) are added to a solution of 80 mg of sodium in 5 ml of methanol and the mixture is heated under reflux for one hour. After addition of 5 ml of acetic acid, it is heated for a further 16 hours. The solvent is removed and the residue is worked up in the customary manner. 3-(2,1,3-Benzothiadiazol-5-yl)-4-benzyl-5-hydroxy-5-(4-methoxy-phenyl)-5H-furan-2-one, FAB 431, is obtained.

후처리

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for one hour
  3. temperatureis heated for a further 16 hours
  4. customThe solvent is removed

출처 및 근거

ORD 기록
ord-7de4d829c5034304a9251f258cd56006
출처 데이터셋
uspto-grants-2000_01
특허 번호
US06017939

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