Sulfuric Acid → HCID 12852684, compound

HRID 1156828Notes

Reaction equation

HRID 1156828 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[CH2:5][N:6]1[C:10](=[O:11])[C:9]([C:12]#[N:13])=[C:8]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=[C:7]12)[CH3:2].[OH:20]S(O)(=O)=O>>[CH2:1]([O:3][C:4](=[O:19])[CH2:5][N:6]1[C:10](=[O:11])[C:9]([C:12]([NH2:13])=[O:20])=[C:8]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=[C:7]12)[CH3:2]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 12852682HCID 12852682, compound

Product 1

HCID 12852684HCID 12852684, compound

Conditions

Temperature
25 °C

Procedure

3-Cyano-1,2-dihydro-2-oxocyclohepta[b]pyrrole-1-acetic acid ethyl ester (2.56 g, described in example 12), was suspended in concentrated H2SO4 (10 ml). The mixture was stirred at 25° C. for 3 hr and then poured into ice water (20 ml). After 5 minutes, the resulting solid was collected on a filter, washed with water and then diethyl ether, air dried and recrystallized from ethanoldiethyl ether to give 1.75 g of 3-(aminocarbonyl)-1,2-dihydro-2-oxocyclohepta[b]pyrrole-1-acetic acid ethyl ester; mp 215°-220° C.; nmr (DMSO-d6) δ1.20 (t,J=7.5 Hz, 3H), 3.25 (broad, 2H), 4.15 (q, J=7.5 Hz, 2H), 5.0 (s, 2H), 7.6 (m, 4H), 9.3 (d, J=10 Hz, 1H); ir (white mineral oil) 3360, 3160, 1743, 1734, 1667, 1590 cm-1 ; uvλmax (MeOH) 276 nm (ε32,100), 232 (17,200), 223 (17,100); Anal Calc for C14H14N2O4 : C, 61.36% H, 5.15% N, 10.21%; Found: C, 61.12% H, 5.26% N, 10.24%.

Workup

  1. waitAfter 5 minutes
  2. customthe resulting solid was collected on a filter
  3. washwashed with water
  4. dry with materialdiethyl ether, air dried
  5. customrecrystallized from ethanoldiethyl ether

Sources & evidence

ORD record
ord-cb3862affec34998817848dc8d158fce
Source dataset
uspto-grants-1982_06
Patent number
US04337265

Reaction notes

Loading…