Octane → Methyl 5-{2-[(oxomethylidene)sulfamoyl]phenyl}furan-2-carboxylate

HRID 623174Notes

Reaction equation

HRID 623174 reaction equation
[C:1]([C:5]1[O:6][C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[S:16]([NH:19][C:20](NCCCC)=[O:21])(=[O:18])=[O:17])=[CH:8][CH:9]=1)([O:3][CH3:4])=[O:2].CCCCCCCC.C(Cl)(Cl)=O>>[C:1]([C:5]1[O:6][C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[S:16]([N:19]=[C:20]=[O:21])(=[O:17])=[O:18])=[CH:8][CH:9]=1)([O:3][CH3:4])=[O:2]

Participants

4

Reactant 3

HCID 356OctaneHCID 6371Phosgene2×HCID 13366175HCID 13366175, compound

Product 1

HCID 13630968Methyl 5-{2-[(oxomethylidene)sulfamoyl]phenyl}furan-2-carboxylate

Procedure

A solution of 19.0 g of the product of Example 2 and 0.1 g of 1,4-diazabicyclo[2.2.2.]octane (DABCO) in 90 ml of dry xylenes was heated to reflux temperature (139°). To this solution was added 3.6 ml of liquid phosgene over a period of about 2 hours, keeping the temperature between 125° and 136° by adjusting the rate of phosgene addition. The reaction mixture was cooled to 25°, and filtered under nitrogen to remove DABCO hydrochloride. The filtrate was concentrated in vacuo to give the title compound as a viscous, moisture-sensitive oil. This material was carried on to the desired products without further purification.

Workup

  1. temperatureto reflux temperature (139°)
  2. customthe temperature between 125° and 136°
  3. temperatureThe reaction mixture was cooled to 25°
  4. filtrationfiltered under nitrogen
  5. customto remove DABCO hydrochloride
  6. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-ca2e9648ebde44c2827b792ac961251a
Source dataset
uspto-grants-1988_09
Patent number
US04773927

Reaction notes

Loading…