Ammonia → HCID 54353063, compound

HRID 744170Notes

Reaction equation

HRID 744170 reaction equation
C([O:9][C@H:10]1[C@@H:14]([O:15]C(=O)C2C=CC=CC=2)[C@H:13]([CH2:24][O:25]C(=O)C2C=CC=CC=2)[O:12][C@H:11]1[N:34]1[CH:41]=[CH:40][C:38](=S)[NH:37][C:35]1=[O:36])(=O)C1C=CC=CC=1.[NH3:42]>>[C@@H:11]1([N:34]2[CH:41]=[CH:40][C:38]([NH2:42])=[N:37][C:35]2=[O:36])[O:12][C@@H:13]([CH2:24][OH:25])[C@H:14]([OH:15])[C@@H:10]1[OH:9]

Participants

3

Reactant 2

HCID 222AmmoniaHCID 22865603HCID 22865603, compound

Product 1

HCID 54353063HCID 54353063, compoundYield 81%

Procedure

Compound 19 (3.68 g, 6.42 mmol) was treated with 200 ml of methanolic ammonia in a bomb at 100° C. for 18 hours. After cooling to room temperature, the solvent was evaporated to dryness and the residue dissolved in water (200 ml). The aqueous solution was extracted successively with CHCl3 and CCl4 (3×100 ml) to remove benzamide and methyl benzoate. The aqueous layer was treated with active charcoal, filtered through Celite®, evaporated to dryness and coevaporated with EtOH. The solid obtained was recrystallized from MeOH to give pure compound 20 (1.36 g, 81%) as white solid: m.p. 206°-207° C. (dec).

Workup

  1. customthe solvent was evaporated to dryness
  2. dissolutionthe residue dissolved in water (200 ml)
  3. extractionThe aqueous solution was extracted successively with CHCl3 and CCl4 (3×100 ml)
  4. customto remove benzamide and methyl benzoate
  5. additionThe aqueous layer was treated with active charcoal
  6. filtrationfiltered through Celite®
  7. customevaporated to dryness
  8. customThe solid obtained
  9. customwas recrystallized from MeOH

Sources & evidence

ORD record
ord-acd0894d4ca6440ab8a53b2b0e0b67f5
Source dataset
uspto-grants-1996_09
Patent number
US05559101

Reaction notes

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