Hydrochloric Acid → HCID 22027379, compound

HRID 2293913Notes

Reaction equation

HRID 2293913 reaction equation
C[Al](C)C.[CH2:5]([O:7][C:8]([C:10]1[C:11]([I:20])=[C:12]([S:16]([NH2:19])(=[O:18])=[O:17])[CH:13]=[CH:14][CH:15]=1)=[O:9])[CH3:6].[CH3:21][C:22]1[N:27]=[C:26]([O:28][CH3:29])[N:25]=[C:24]([NH:30][C:31](=O)[O:32]C)[N:23]=1.Cl>CCCCCC.ClCCl>[I:20][C:11]1[C:12]([S:16]([NH:19][C:31]([NH:30][C:24]2[N:25]=[C:26]([O:28][CH3:29])[N:27]=[C:22]([CH3:21])[N:23]=2)=[O:32])(=[O:18])=[O:17])=[CH:13][CH:14]=[CH:15][C:10]=1[C:8]([O:7][CH2:5][CH3:6])=[O:9]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14404501Methyl (4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamateHCID 16682925TrimethylaluminumHCID 21473067HCID 21473067, compound

Product 1

HCID 22027379HCID 22027379, compoundYield 32.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8058HexaneSolvent

Procedure

14 mmol of trimethylaluminum (7 ml of a 2M solution in hexane) are added dropwise under a nitrogen protective atmosphere to a suspension of 3.6 g of 3-ethoxycarbonyl-2-iodobenzenesulfonamide in 100 ml of absolute dichloromethane. The mixture is stirred at room temperature for 30 minutes, and 2.2 g of O-methyl (4-methyl-6-methoxy-1,3,5-triazin-2-yl)carbamate in 25 ml of dichloromethane are then added, and the mixture is refluxed for 13 hours. The solution is cooled to room temperature, 25 ml of 2N hydrochloric acid are added dropwise with ice-cooling, and the hydrochloric acid phase is extracted twice using dichloromethane. The organic phase is concentrated in vacuo, and the residue is treated with acetone and 100 ml of 10% aqueous sodium acetate solution. The mixture is stirred for 3 hours and then filtered off with suction, followed by a washing step with diethyl ether, the aqueous phase is brought to pH 2-3 using concentrated hydrochloric acid and stirred for 15 minutes, and the product is filtered off with suction. After drying in vacuo at 50° C., 1.7 g of ethyl 2-iodo-3-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl]amino]sulfonyl]benzoate of m.p. 177°-9° C. are obtained.

Workup

  1. temperaturethe mixture is refluxed for 13 hours
  2. temperatureThe solution is cooled to room temperature
  3. temperaturecooling
  4. extractionthe hydrochloric acid phase is extracted twice using dichloromethane
  5. concentrationThe organic phase is concentrated in vacuo
  6. additionthe residue is treated with acetone and 100 ml of 10% aqueous sodium acetate solution
  7. stirringThe mixture is stirred for 3 hours
  8. filtrationfiltered off with suction
  9. stirringstirred for 15 minutes
  10. filtrationthe product is filtered off with suction
  11. customAfter drying in vacuo at 50° C.

Sources & evidence

ORD record
ord-9a68a1fce72440448a33c9316d8571cb
Source dataset
uspto-grants-1997_11
Patent number
US05688745

Reaction notes

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