Water → HCID 178429693, compound

HRID 1838679Notes

Reaction equation

HRID 1838679 reaction equation
[CH3:1][S:2]([C:5]1[C:13]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:12][C:8]([C:9](Cl)=[O:10])=[C:7]([CH3:18])[CH:6]=1)(=[O:4])=[O:3].[NH2:19][C:20]([NH2:22])=[NH:21].O>CN(C=O)C>[CH3:1][S:2]([C:5]1[C:13]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:12][C:8]([C:9]([NH:21][C:20]([NH2:22])=[NH:19])=[O:10])=[C:7]([CH3:18])[CH:6]=1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 962WaterHCID 3520GuanidineHCID 110882142-Methyl-4,5-di(methylsulfonyl)benzoyl chloride

Product 1

HCID 178429693HCID 178429693, compoundYield 64.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4,5-bismethanesulfonyl-2-methylbenzoyl chloride, prepared as described in 2.1., in 5 l of DMF is added dropwise at 12° to the guanidine solution prepared as described in 2.2. The reaction mixture is stirred at 20° for 5 hours, and 45 l of cold water (0-50) are added slowly. The deposited crystals are filtered off and rinsed with ice-water, acetonitrile and diethyl ether. The crude crystals are dissolved in 315 l of hot acetonitrile/water (20:1). The solution is treated with 200 g of activated carbon, filtered and cooled to 0°, giving N-(4,5-bismethanesulfonyl-2-methylbenzoyl)guanidine as the acetonitrile adduct in a yield of 64.8%; m.p. 233-2340 °.

Workup

  1. customprepared
  2. filtrationThe deposited crystals are filtered off
  3. washrinsed with ice-water, acetonitrile and diethyl ether
  4. dissolutionThe crude crystals are dissolved in 315 l of hot acetonitrile/water (20:1)
  5. additionThe solution is treated with 200 g of activated carbon
  6. filtrationfiltered
  7. temperaturecooled to 0°

Sources & evidence

ORD record
ord-f9c376fa2fc14ccf891389a3f80d8a0b
Source dataset
uspto-grants-2004_01
Patent number
US06673968B1

Reaction notes

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