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

HRID 1585199Notes

Reaction equation

HRID 1585199 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[N:5]=[C:4]([CH3:10])[N:3]=1.[C:11](=O)(OC1C=CC=CC=1)[O:12]C1C=CC=CC=1.[NH2:27][S:28]([C:31]1[CH:40]=[C:39]([I:41])[CH:38]=[CH:37][C:32]=1[C:33]([O:35][CH3:36])=[O:34])(=[O:30])=[O:29]>CC(N(C)C)=O>[CH3:9][O:8][C:6]1[N:5]=[C:4]([CH3:10])[N:3]=[C:2]([NH:1][C:11]([NH:27][S:28]([C:31]2[CH:40]=[C:39]([I:41])[CH:38]=[CH:37][C:32]=2[C:33]([O:35][CH3:36])=[O:34])(=[O:30])=[O:29])=[O:12])[N:7]=1

Participants

5

Reactant 3

HCID 7597Diphenyl carbonateHCID 154662-Amino-4-methoxy-6-methyl-1,3,5-triazineHCID 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)benzoateYield 58%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent3×

Procedure

0.96 g of sodium tert-butylate was added to a suspension of 1.05 g of 2-amino-4-methoxy-6-methyl-1,3,5-triazine in 20 ml of dimethylacetamide (DMA) at room temperature, with vigorous stirring, to form a first mixture. A solution of 1.12 g of diphenyl carbonate in 10 ml of DMA was then added to the first mixture, in the course of 7 minutes, while it was cooled in an ice bath, to form a second mixture. The second mixture was subsequently stirred for another 15 minutes while cooled in the ice bath, and a solution of 1.84 g of methyl 2-aminosulfonyl-4-iodobenzoate (92.5% pure) in DMA was then added dropwise in the course of 7 minutes. When the reaction ended, the product was worked up as described in Example 1. 1.47 g of the desired product (58% of theory) was thus obtained.

Workup

  1. customto form a first mixture
  2. temperaturewas cooled in an ice bath
  3. customto form a second mixture

Sources & evidence

ORD record
ord-6fa91af6c2cf4a889404f993fcbd251c
Source dataset
uspto-grants-1999_08
Patent number
US05936085

Reaction notes

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