Hydrochloric Acid → HCID 20244112, compound

HRID 482896Notes

Reaction equation

HRID 482896 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]2[CH:8]=[N:9][NH:10][C:5]2=[C:4]([NH:11][C:12]2[CH:20]=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[CH:14][CH:13]=2)[CH:3]=1.Cl.CS(C)=O.[CH2:26](O)[CH3:27]>>[C:16]([C:15]1[CH:19]=[CH:20][C:12]([NH:11][C:4]2[CH:3]=[C:2]([CH3:1])[N:7]=[C:6]3[CH:8]=[N:9][NH:10][C:5]=23)=[CH:13][CH:14]=1)([O:18][CH2:26][CH3:27])=[O:17]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 679Dimethyl SulfoxideHCID 702Ethanol2×HCID 20244119HCID 20244119, compound

Product 1

HCID 20244112HCID 20244112, compound

Procedure

The carboxylic acid (E2) of Example 2 (0.5 g, 0.0019 mole) was heated at reflux in ethanol (25 ml) to which several drops of a saturated ethanol solution of hydrogen chloride had been added. Dimethyl sulphoxide (5.5 ml) was added after 11/2 h to aid solution and heating continued for a further 71/4 h. The solution was filtered and solvent removed under reduced pressure. Ether and a small amount of ethyl acetate were added and the resulting yellow solid (518 mg, 94%) collected, m.p. 247°-250° C.

Workup

  1. additionhad been added
  2. temperatureheating
  3. custom4 h
  4. filtrationThe solution was filtered
  5. customsolvent removed under reduced pressure
  6. additionEther and a small amount of ethyl acetate were added
  7. customthe resulting yellow solid (518 mg, 94%) collected

Sources & evidence

ORD record
ord-30e7513152dc4a32bce43f1c71a3ed92
Source dataset
uspto-grants-1986_03
Patent number
US04576952

Reaction notes

Loading…