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

HRID 1795367Notes

Reaction equation

HRID 1795367 reaction equation
[I:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([S:12]([N:15]=[C:16]=[O:17])(=[O:14])=[O:13])[CH:3]=1.[NH2:18][C:19]1[N:24]=[C:23]([O:25][CH3:26])[N:22]=[C:21]([CH3:27])[N:20]=1>C1(C)C(C)=CC=CC=1.C(OCC)(=O)C>[I:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([S:12]([NH:15][C:16]([NH:18][C:19]2[N:24]=[C:23]([O:25][CH3:26])[N:22]=[C:21]([CH3:27])[N:20]=2)=[O:17])(=[O:14])=[O:13])[CH:3]=1

Participants

5

Reactant 2

HCID 154662-Amino-4-methoxy-6-methyl-1,3,5-triazineHCID 11326070Methyl 4-iodo-2-isocyanatosulfonylbenzoate

Product 1

HCID 11027582Methyl 4-iodo-2-(3-(4-methoxy-6-methyl-1,3,5-triazine-2-yl)ureidosulfonyl)benzoateYield 99.2%

Reagents, catalysts & solvents 2

HCID 7237O-XyleneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Under protective gas, a 14.5% strength solution (1465 g) of methyl 4-iodo-2-isocyanatosulfonylbenzoate in xylene is added over 4 hours at a constant rate at 50° C. to a suspension of 84.5 g of 2-amino-4-methoxy-6-methyl-1,3,5-triazine in 670 g of ethyl acetate. After the addition has ended, the mixture is stirred at the same temperature for approximately 4 hours, and the ethyl acetate is then distilled off under reduced pressure (80–60 mbar, T=50° C.). The suspension that remains is filtered off with suction and the solid is washed repeatedly with dilute hydrochloric acid and dried; if appropriate, acetone can be added to the hydrochloric acid. This gives 297 g (content>98%) of the title compound; yield 99.2% of theory.

Workup

  1. additionAfter the addition
  2. distillationthe ethyl acetate is then distilled off under reduced pressure (80–60 mbar, T=50° C.)
  3. filtrationThe suspension that remains is filtered off with suction
  4. washthe solid is washed repeatedly with dilute hydrochloric acid
  5. customdried
  6. additionif appropriate, acetone can be added to the hydrochloric acid

Sources & evidence

ORD record
ord-19ac6c5ba18744269ddda3b91ec7f282
Source dataset
uspto-grants-2006_04
Patent number
US07026477B1

Reaction notes

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