Ammonia → HCID 135744107, compound

HRID 865924Notes

Reaction equation

HRID 865924 reaction equation
[NH3:1].[C:2]1([CH2:8][O:9][C:10](=[O:29])[NH:11][CH:12](SC(C)C)[C:13]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:22](=O)[CH3:23])=[O:14])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1COCC1.[Hg](Cl)Cl>[CH3:23][C:22]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[NH:15][C:13](=[O:14])[CH:12]([NH:11][C:10](=[O:29])[O:9][CH2:8][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[N:1]=1

Participants

5

Reactant 2

HCID 222Ammonia2×HCID 23373644HCID 23373644, compound

Product 1

HCID 135744107HCID 135744107, compound

Reagents, catalysts & solvents 2

HCID 24085Mercuric ChlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Ammonia gas was passed through a solution of phenylmethyl[2-[(2-acetylphenyl)amino]-1-[(1-methylethyl)thio]-2-oxoethyl]carbamate (14.74 g) in dry THF (250 ml) at 0° for 0.5 h. Mercury (II) chloride (10.00 g) was added and the mixture was rapidly stirred for 6 h whilst continuing to pass ammonia gas through the mixture. The mixture was filtered through hyflo and the solvent removed from the filtrate by evaporation in vacuo. The residue was treated with acetic acid (290 ml) and sodium acetate (13.35 g) and the resulting mixture stirred at 23° for 18 h. The solvent was evaporated in vacuo and the residue was purified by chromatography. Elution with EA gave the title compound (5.70 g).

Workup

  1. filtrationThe mixture was filtered through hyflo
  2. customthe solvent removed from the filtrate by evaporation in vacuo
  3. additionThe residue was treated with acetic acid (290 ml) and sodium acetate (13.35 g)
  4. stirringthe resulting mixture stirred at 23° for 18 h
  5. customThe solvent was evaporated in vacuo
  6. customthe residue was purified by chromatography
  7. washElution with EA

Sources & evidence

ORD record
ord-fd96eeaa4f7f4b4b96f6efa902913de0
Source dataset
uspto-grants-1996_10
Patent number
US05569654

Reaction notes

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