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

HRID 1585198Notes

Reaction equation

HRID 1585198 reaction equation
C[C:2]([O-:5])(C)C.[K+].[NH2:7][C:8]1[N:13]=[C:12]([O:14][CH3:15])[N:11]=[C:10]([CH3:16])[N:9]=1.C(=O)(OC1C=CC=CC=1)OC1C=CC=CC=1.[NH2:33][S:34]([C:37]1[CH:46]=[C:45]([I:47])[CH:44]=[CH:43][C:38]=1[C:39]([O:41][CH3:42])=[O:40])(=[O:36])=[O:35]>CC(N(C)C)=O>[CH3:15][O:14][C:12]1[N:11]=[C:10]([CH3:16])[N:9]=[C:8]([NH:7][C:2]([NH:33][S:34]([C:37]2[CH:46]=[C:45]([I:47])[CH:44]=[CH:43][C:38]=2[C:39]([O:41][CH3:42])=[O:40])(=[O:36])=[O:35])=[O:5])[N:13]=1

Participants

6

Reactant 4

HCID 7597Diphenyl carbonateHCID 154662-Amino-4-methoxy-6-methyl-1,3,5-triazineHCID 109478222-(Aminosulfonyl)-4-iodobenzoic acid methyl esterHCID 23665647Potassium tert-butoxide

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

2.59 g of potassium tert-butylate was added to a suspension of 2.85 g of 2-amino-4-methoxy-6-methyl-1,3,5-triazine in 40 ml of dimethylacetamide (DMA) at room temperature to form a first mixture. A solution of 4.94 g of diphenyl carbonate in 20 ml of DMA was then added dropwise to the first mixture at about 5° C. to form a second mixture. The second mixture was subsequently added dropwise to a solution of 5.00 g of methyl 2-aminosulfonyl-4-iodobenzoate (92.5% pure) in 15 ml of DMA at about 5° C., to form a third mixture. When the reaction ended, the third mixture was filtered over kieselguhr (®Celite). The filtrate was introduced into a solution of 200 ml of ice-water and 10 ml of concentrated hydrochloric acid, whereby the crude urea product separated out. The crude product which separated out was then purified by stirring with methanol and diisopropyl ether and dried. The yield was 4.50 g (66% of theory).

Workup

  1. customto form a first mixture
  2. customto form a second mixture
  3. customto form a third mixture
  4. filtrationthe third mixture was filtered over kieselguhr (®Celite)
  5. additionThe filtrate was introduced into a solution of 200 ml of ice-water and 10 ml of concentrated hydrochloric acid, whereby the crude urea product
  6. customseparated out
  7. customThe crude product which separated out
  8. customwas then purified
  9. customdried

Sources & evidence

ORD record
ord-03ba43a6334546a5a202ae429f3f7516
Source dataset
uspto-grants-1999_08
Patent number
US05936085

Reaction notes

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