Hydrochloric Acid → Methyl 2-[[[4-(1-carboxyethoxy)-6-methyl-1,3,5-triazin-2-yl]aminocarbonyl]aminosulfonyl]benzoate

HRID 463988

반응식

HRID 463988 반응식
[N:1]([S:4]([C:7]1[CH:16]=[CH:15][CH:14]=[CH:13][C:8]=1[C:9]([O:11][CH3:12])=[O:10])(=[O:6])=[O:5])=[C:2]=[O:3].[NH2:17][C:18]1[N:23]=[C:22]([CH3:24])[N:21]=[C:20]([O:25][CH:26]([CH3:32])[C:27]([O:29]CC)=[O:28])[N:19]=1.S(N=C=O)(N=C=O)(=O)=O.[OH-].[Na+].Cl>C(Cl)Cl.O>[C:27]([CH:26]([O:25][C:20]1[N:21]=[C:22]([CH3:24])[N:23]=[C:18]([NH:17][C:2]([NH:1][S:4]([C:7]2[CH:16]=[CH:15][CH:14]=[CH:13][C:8]=2[C:9]([O:11][CH3:12])=[O:10])(=[O:6])=[O:5])=[O:3])[N:19]=1)[CH3:32])([OH:29])=[O:28]

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 77898Sulphonyl diisocyanate2회HCID 156281Benzoic acid, 2-(isocyanatosulfonyl)-, methyl esterHCID 19881799Ethyl 2-[(4-amino-6-methyl-1,3,5-triazin-2-yl)oxy]propanoate

생성물 1

HCID 13646750Methyl 2-[[[4-(1-carboxyethoxy)-6-methyl-1,3,5-triazin-2-yl]aminocarbonyl]aminosulfonyl]benzoate수율 23.8%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

Methyl 2-(isocyanatosulfonyl)benzoate (10.1 g) and 8.0 g of ethyl 2-[(4-amino-6-methyl-1,3,5-triazin-2-yl)oxy]propanoate were stirred in 80 ml of methylene chloride at ambient temperature for 18 hours. An additional 2 g of the sulfonylisocyanate was added and the reaction mixture was stirred for four more hours and then 2 g more of the sulfonylisocyanate was added. After stirring for four more hours at ambient temperature, 400 ml of water was added and the pH of this mixture was adjusted to pH 8 by the addition of 10% aqueous sodium hydroxide. The aqueous phase was separated and acidified to pH 1 with hydrochloric acid to precipitate a thick white gum. Sufficient 50% aqueous sodium hydroxide was added to achieve pH 12 and the mixture was heated on a steam bath until a clear solution resulted. The solution was again acidified with hydrochloric acid to pH 3 and the resultant cloudy solution was extracted with dichlormethane. The organic phase was dried and the solvent was removed to afford 3.7 g of the title compound as a glass.

후처리

  1. stirringAfter stirring for four more hours at ambient temperature
  2. customThe aqueous phase was separated
  3. customto precipitate a thick white gum
  4. additionSufficient 50% aqueous sodium hydroxide was added
  5. temperaturethe mixture was heated on a steam bath until a clear solution
  6. customresulted
  7. extractionthe resultant cloudy solution was extracted with dichlormethane
  8. customThe organic phase was dried
  9. customthe solvent was removed

출처 및 근거

ORD 기록
ord-33ed3249c4dc42189aec440957359bd9
출처 데이터셋
uspto-grants-1985_10
특허 번호
US04545808

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