Methanesulfonic Acid → HCID 15097348, compound

HRID 1586610Notes

Reaction equation

HRID 1586610 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](Cl)=[O:7].[S:9]([C:13]1[CH:14]=[C:15]([NH:19][C:20]([N:22]([CH3:24])[CH3:23])=[O:21])[CH:16]=[CH:17][CH:18]=1)(=[O:12])(=[O:11])[NH2:10].C(N(CC)CC)C.CS(O)(=O)=O>CN(C)C1C=CN=CC=1.C(#N)C.O>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([NH:10][S:9]([C:13]1[CH:14]=[C:15]([NH:19][C:20]([N:22]([CH3:24])[CH3:23])=[O:21])[CH:16]=[CH:17][CH:18]=1)(=[O:11])=[O:12])=[O:7]

Participants

8

Reactant 4

HCID 6395Methanesulfonic AcidHCID 8471TriethylamineHCID 682422-Furancarbonyl chlorideHCID 19758586HCID 19758586, compound

Product 1

HCID 15097348HCID 15097348, compoundYield 80.7%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

6.1 g of 2-furancarboxylic acid chloride and 0.1 g of 4-dimethylaminopyridine are added to a suspension of 10.1 g of 1-(3-sulfamoylphenyl)-3,3-dimethylurea in 60 ml of acetonitrile. 9.5 g of triethylamine are added dropwise to that mixture at room temperature. The reaction mixture is stirred for 15 hours at room temperature and for one hour at 60° C. After the mixture has cooled, 4.5 g of methanesulfonic acid are added dropwise thereto and the mixture is taken up in 1 liter of water. The oil that separates out crystallises after a short time. The crystals are separated off, washed with methanol and dried, yielding 11.3 g of 1-[3-(N-2-furylcarbonylsulfamoyl)-phenyl]-3,3-dimethylurea, m.p. 216°-217° C. (with decomposition).

Workup

  1. temperatureAfter the mixture has cooled
  2. customThe oil that separates out crystallises after a short time
  3. customThe crystals are separated off
  4. washwashed with methanol
  5. customdried

Sources & evidence

ORD record
ord-6f6b0d971a4742a886da5839a070fbc3
Source dataset
uspto-grants-1993_06
Patent number
US05215570

Reaction notes

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