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

HRID 1585200Notes

Reaction equation

HRID 1585200 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 63.8%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent3×

Conditions

Temperature
5 °C

Procedure

5.09 g of sodium tert-butylate was added to a suspension of 3.69 g of 2-amino-4-methoxy-6-methyl-1,3,5-triazine in 100 ml of DMA at room temperature. After cooling to 3-7° C., a solution of 5.64 g of diphenyl carbonate and 50 ml of DMA was added dropwise, to form a reaction mixture. The reaction mixture was then stirred at that temperature for 15 minutes. The reaction mixture was then added dropwise to a solution of 8.85 g of methyl 2-aminosulfonyl-4-iodobenzoate and 50 ml of DMA at 3-7° C., to form a resulting mixture which was stirred at 3° C. for 1 hour and at room temperature for 2 hours. The volatile components were then distilled off under reduced pressure. The residue was dissolved in 250 ml of water and acidified with concentrated hydrochloric acid (pH=2-3) whereby the crude product separated out. The crude product which separated out was washed with methanol and diisopropyl ether. After drying, 8.4 g of the desired product (purity>92%) was obtained.

Workup

  1. customto form a reaction mixture
  2. customto form a resulting mixture which
  3. stirringwas stirred at 3° C. for 1 hour and at room temperature for 2 hours
  4. distillationThe volatile components were then distilled off under reduced pressure
  5. dissolutionThe residue was dissolved in 250 ml of water
  6. customseparated out
  7. customThe crude product which separated out
  8. washwas washed with methanol and diisopropyl ether
  9. customAfter drying

Sources & evidence

ORD record
ord-0b34e457a4bc402ebebfbada2ff7b4d0
Source dataset
uspto-grants-1999_08
Patent number
US05936085

Reaction notes

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