Methanol → HCID 67654054, compound

HRID 1459445Notes

Reaction equation

HRID 1459445 reaction equation
S(Cl)(Cl)=O.[OH:5][C:6]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][C:7]=1[C:8]([NH:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[O:9].[CH3:22]O>>[OH:5][C:6]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][C:7]=1[C:8]([NH:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH3:22])=[O:15])=[O:9]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 9859555HCID 9859555, compound

Product 1

HCID 67654054HCID 67654054, compound

Procedure

After dropwise adding 8.5 g (71 mmol) of thionyl chloride to 30 ml of anhydrous methanol at 10° C. during 30 minutes under cooling by ice while stirring, the solution was stirred at the same temperature for additional 45 minutes, then 5.1 g (20 mmol) of 4-[N-(2,5-dihydroxybenzoyl)amino]butyric acid (compound of Example 36) were portionwise added. The reaction mixture was allowed to warm to room temperature and stirred at 80° C. for 8 hours. After filtering the precipitate by and washing with methanol 3.7 g (68%) of the aimed compound were obtained, m.p.: 155°-159° C.

Workup

  1. temperatureunder cooling by ice
  2. stirringthe solution was stirred at the same temperature for additional 45 minutes
  3. stirringstirred at 80° C. for 8 hours
  4. filtrationAfter filtering the precipitate by and
  5. washwashing with methanol 3.7 g (68%) of the aimed compound
  6. customwere obtained

Sources & evidence

ORD record
ord-8864a5f21bd1453b852a7832f178707e
Source dataset
uspto-grants-1998_12
Patent number
US05854250

Reaction notes

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