Hydrochloric Acid → Methyl 4-iodo-2-(3-(4-methoxy-6-methyl-1,3,5-triazine-2-yl)ureidosulfonyl)benzoate

HRID 1585201Notes

Reaction equation

HRID 1585201 reaction equation
[H-].[Na+].[NH2:3][C:4]1[N:9]=[C:8]([O:10][CH3:11])[N:7]=[C:6]([CH3:12])[N:5]=1.[C:13](=O)(OC1C=CC=CC=1)[O:14]C1C=CC=CC=1.[NH2:29][S:30]([C:33]1[CH:42]=[C:41]([I:43])[CH:40]=[CH:39][C:34]=1[C:35]([O:37][CH3:38])=[O:36])(=[O:32])=[O:31].Cl>CC(N(C)C)=O>[CH3:11][O:10][C:8]1[N:7]=[C:6]([CH3:12])[N:5]=[C:4]([NH:3][C:13]([NH:29][S:30]([C:33]2[CH:42]=[C:41]([I:43])[CH:40]=[CH:39][C:34]=2[C:35]([O:37][CH3:38])=[O:36])(=[O:32])=[O:31])=[O:14])[N:9]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 7597Diphenyl carbonateHCID 154662-Amino-4-methoxy-6-methyl-1,3,5-triazineHCID 24758Sodium hydrideHCID 109478222-(Aminosulfonyl)-4-iodobenzoic acid methyl ester

Product 1

HCID 11027582Methyl 4-iodo-2-(3-(4-methoxy-6-methyl-1,3,5-triazine-2-yl)ureidosulfonyl)benzoate

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent3×

Procedure

0.084 g of sodium hydride (60% pure in paraffin oil) was added to a suspension of 0.23 g of 2-amino-4-methoxy-6-methyl-1,3,5-triazine in 3 ml of dimethylacetamide (DMA) at room temperature to form a mixture. The mixture was stirred until the evolution of gas ended. A solution of 0.44 g of diphenyl carbonate in 1 ml of DMA was then slowly added dropwise at about 5° C., and the resulting mixture therefrom was stirred for 10 minutes. A solution of 0.68 g of methyl 2-aminosulfonyl-4-iodobenzoate (92.5% pure) in 2 ml of DMA was slowly added dropwise, to the resulting mixture, while cooled in an ice bath, to form a reaction mixture. When the reaction ended, the reaction mixture was then introduced into a solution of 30 ml of ice-water and 0.25 ml of concentrated hydrochloric acid, whereby a crude product separated out. The crude product which separated out was then purified by washing with a little water, methanol and diisopropyl ether and drying. The yield was 0.47 g (46% of theory).

Workup

  1. customto form a mixture
  2. stirringthe resulting mixture therefrom was stirred for 10 minutes
  3. temperaturewhile cooled in an ice bath
  4. customto form a reaction mixture
  5. customseparated out
  6. customThe crude product which separated out
  7. customwas then purified
  8. washby washing with a little water, methanol and diisopropyl ether
  9. customdrying

Sources & evidence

ORD record
ord-08298b58efe14f4ebde324485fcc7fbe
Source dataset
uspto-grants-1999_08
Patent number
US05936085

Reaction notes

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