Ethyl Methanesulfonate → HCID 178477473, compound

HRID 863465Notes

Reaction equation

HRID 863465 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][CH:21]=1)[CH2:5][NH:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]([NH2:18])=[S:17])=[CH:11][CH:10]=1.[CH3:22][S:23]([OH:26])(=[O:25])=[O:24].[CH3:27][S:28]([O:31][CH2:32][CH3:33])(=[O:30])=[O:29]>C(O)C>[CH3:22][S:23]([OH:26])(=[O:25])=[O:24].[CH3:27][S:28]([OH:31])(=[O:30])=[O:29].[CH2:32]([S:17][C:16](=[NH:18])[NH:15][C:12]1[CH:11]=[CH:10][C:9]([CH2:8][CH2:7][NH:6][CH2:5][C:4]2[CH:19]=[CH:20][CH:21]=[C:2]([Cl:1])[CH:3]=2)=[CH:14][CH:13]=1)[CH3:33]

Participants

5

Reactant 3

HCID 6113Ethyl Methanesulfonate2×HCID 6395Methanesulfonic AcidHCID 19696463HCID 19696463, compound

Product 1

HCID 178477473HCID 178477473, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred mixture of the product of step (e) (272.5 mg, 0.852 mmol) and ethanol (2.6 ml) was added methanesulfonic acid (81.88 mg, 0.852 mmol). After stirring for a few minutes, ethyl methanesulfonate (211.6 mg, 1.70 mmol) was added. The reaction mixture was refluxed, with stirring, for 3 hours. Additional ethyl methanesulfonate (117 mg) was added and refluxing continued for 2 hours to complete the reaction. On cooling, the product crystallized to a thick mass. Ether was added and the product was isolated by filtration and then recrystallized from ethanol-ether to yield 407.3 mg of N-(4-(2-(3-chlorobenzylamino)ethyl)phenyl)carbamimidothioic acid ethyl ester dimethanesulfonate, m.p. 173°-5° C.

Workup

  1. temperatureThe reaction mixture was refluxed
  2. stirringwith stirring, for 3 hours
  3. temperaturerefluxing
  4. customthe reaction
  5. temperatureOn cooling
  6. customthe product crystallized to a thick mass
  7. additionEther was added
  8. customthe product was isolated by filtration
  9. customrecrystallized from ethanol-ether

Sources & evidence

ORD record
ord-45d90190b9f446b1859a81fae2b733b5
Source dataset
uspto-grants-1998_02
Patent number
US05721247

Reaction notes

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