Ammonia → HCID 135972002, compound

HRID 904668Notes

Reaction equation

HRID 904668 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 880 ammonia 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-662bfacc925842ed84e59bd45eb06653
Source dataset
uspto-grants-1983_12
Patent number
US04419352

Reaction notes

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