Hydrochloric Acid → HCID 18973664, compound

HRID 2394471Notes

Reaction equation

HRID 2394471 reaction equation
[CH2:1](I)[CH3:2].[CH2:4]([C:6]1[C:7](=[O:31])[N:8]([C:12]([NH:14][CH2:15][CH:16]2[C:25]3[C:20](=[CH:21][C:22]([OH:30])=[C:23]([S:26](=[O:29])(=[O:28])[NH2:27])[CH:24]=3)[O:19][CH2:18][CH2:17]2)=[O:13])[CH2:9][C:10]=1[CH3:11])[CH3:5].C(=O)([O-])[O-].[K+].[K+].Cl>CC(C)=O>[CH2:4]([C:6]1[C:7](=[O:31])[N:8]([C:12]([NH:14][CH2:15][CH:16]2[C:25]3[C:20](=[CH:21][C:22]([O:30][CH2:1][CH3:2])=[C:23]([S:26](=[O:28])(=[O:29])[NH2:27])[CH:24]=3)[O:19][CH2:18][CH2:17]2)=[O:13])[CH2:9][C:10]=1[CH3:11])[CH3:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 18973644HCID 18973644, compound

Product 1

HCID 18973664HCID 18973664, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2.16 ml (0.027 mol) of ethyl iodide are added to a suspension of 9 g (0.022 mol) of 4-((3-ethyl-4-methyl-2-oxo-3-pyrroline-1-carboxamido)-methyl)-6-sulfamoyl-7-hydroxychroman and 6.1 g (0.044 mol) of potassium carbonate in 60 ml of acetone. After stirring under reflux for three hours, the mixture is introduced into ice/water and cautiously acidified with concentrated hydrochloric acid. The precipitate is filtered off with suction, washed several times with cold water, dried and recrystallized from ethanol/DMF. 4-((3-Ethyl-4-methyl-2-oxo-3-pyrroline-1-carboxamido)-methyl)-6-sulfamoyl-7-ethoxychroman of melting point 192° C. is obtained.

Workup

  1. temperatureunder reflux for three hours
  2. filtrationThe precipitate is filtered off with suction
  3. washwashed several times with cold water
  4. customdried
  5. customrecrystallized from ethanol/DMF

Sources & evidence

ORD record
ord-ee799225916b45f580cd33947267d820
Source dataset
uspto-grants-1998_09
Patent number
US05811448

Reaction notes

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