Ammonia → HCID 135972002, compound

HRID 223703Notes

Reaction equation

HRID 223703 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[C:12]([CH2:15][CH2:16][CH3:17])[C:13]=1[OH:14])[N:10]=[C:9]([C:18]([OH:20])=[O:19])[CH:8]=[C:7]2[NH:21][CH3:22])(=[O:3])[CH3:2].Cl.N.[CH2:25](O)[CH3:26]>>[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[C:12]([CH2:15][CH2:16][CH3:17])[C:13]=1[OH:14])[N:10]=[C:9]([C:18]([O:20][CH2:25][CH3:26])=[O:19])[CH:8]=[C:7]2[NH:21][CH3:22])(=[O:3])[CH3:2]

Participants

5

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 702EthanolHCID 136024919HCID 136024919, compound

Product 1

HCID 135972002HCID 135972002, compound

Procedure

The crude product of step (d) (6.4 g) in ethanol (500 mls) which had been previously saturated with hydrogen chloride gas was heated under reflux for 1 hour. The reaction mixture was cooled, made basic with conc. aqueous ammonia solution and extracted with ethyl acetate, which was then washed with water and dried over magnesium sulphate. The solvent was removed by evaporation to leave 8.0 g of residual yellow solid. This solid was recrystallised from ethanol to give 3.8 g of yellow needles mp 219°-220°.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 hour
  3. temperatureThe reaction mixture was cooled
  4. extractionextracted with ethyl acetate, which
  5. washwas then washed with water
  6. dry with materialdried over magnesium sulphate
  7. customThe solvent was removed by evaporation

Sources & evidence

ORD record
ord-d2aff3f25dca4786bd947458c53860ce
Source dataset
uspto-grants-1982_10
Patent number
US04356181

Reaction notes

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