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

HRID 619917

Reaction equation

HRID 619917 reaction equation
[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]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 77898Sulphonyl diisocyanate2×HCID 156281Benzoic acid, 2-(isocyanatosulfonyl)-, methyl esterHCID 19881799Ethyl 2-[(4-amino-6-methyl-1,3,5-triazin-2-yl)oxy]propanoate

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

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 dichloromethane. The organic phase was dried and the solvent was removed to afford 3.7 g of the title compound as a glass.

Workup

  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 dichloromethane
  8. customThe organic phase was dried
  9. customthe solvent was removed

Sources & evidence

ORD record
ord-8ab245fc621c41f2a8b4d66645024d37
Source dataset
uspto-grants-1989_04
Patent number
US04818278

Linked notes

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