Acetic Acid → HCID 20130082, compound

HRID 845721Notes

Reaction equation

HRID 845721 reaction equation
Cl[CH:2]([O:4][C:5]([NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=1)=[O:6])[CH3:3].[C:20]([OH:23])(=[O:22])[CH3:21]>>[C:20]([O:23][CH:2]([O:4][C:5]([NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=1)=[O:6])[CH3:3])(=[O:22])[CH3:21]

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 20130080HCID 20130080, compound

Product 1

HCID 20130082HCID 20130082, compound

Procedure

The chloroethyl carbamate from Example 11 (0.25 g) was dissolved in acetic acid (25 ml) and mercuric acetate (1.0 g) was added to it. The reaction mixture was stirred at room temperature for 3 hours. It was filtered and the filtrate was evaporated in vacuum at room temperature. The residue was dissolved in ether and filtered. Evaporation of ether gave a thick oil weighing 0.21 g as a practically pure compound. An analytical sample was prepared by filtering through silica gel in chloroform. NMR (CDCl3) δ1.45 (3H, d, J=7 Hz, CH3CH), 2.06 (3H, s, OAc), 2.76 (2H, t, J=7 Hz), ArCH2), 3.38 (2H, t, J=7 Hz, NHCH2), 3.9 (6H, s, OMe), 5.06 (1H, broad t, NH) and 6.6-7.0 (4H, CHCH3 and aromatic). IR (film) ν3345, 1742, 1723, 1515, 1262, 1238 cm-1. m/e 311 (M+), 207, 164, 151, etc.

Workup

  1. filtrationIt was filtered
  2. customthe filtrate was evaporated in vacuum at room temperature
  3. dissolutionThe residue was dissolved in ether
  4. filtrationfiltered
  5. customEvaporation of ether
  6. customgave a thick oil
  7. customAn analytical sample was prepared
  8. filtrationby filtering through silica gel in chloroform

Sources & evidence

ORD record
ord-bd9afb08bed94ee7a2f6b43c3271d87b
Source dataset
uspto-grants-1988_07
Patent number
US04760057

Reaction notes

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