Imidazole → HCID 54180136, compound

HRID 1904151Notes

Reaction equation

HRID 1904151 reaction equation
[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24]([C:26](=[N:30][O:31][CH2:32][CH2:33]I)[C:27]([OH:29])=[O:28])[N:25]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC(Cl)C.[NH:39]1[CH:43]=[CH:42][N:41]=[CH:40]1.C(OC(C)C)(C)C>CC(N(C)C)=O>[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24]([C:26](=[N:30][O:31][CH2:32][CH2:33][N:39]2[CH:43]=[CH:42][N:41]=[CH:40]2)[C:27]([OH:29])=[O:28])[N:25]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 63651,1-DichloroethaneHCID 7914Diisopropyl EtherHCID 53951774HCID 53951774, compound

Product 1

HCID 54180136HCID 54180136, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent2×

Procedure

A mixture of 3 g of the syn isomer of 2-(2-tritylamino-4-thiazolyl)-2-(2-iodoethoxyimino)-acetic acid solvated with dichloroethane (=2.56 g of pure acid), 4.2 g of imidazole and 10 ml of dimethylacetamide was stirred for 3 hours at room temperature and after addition of another 10 ml of dimethylacetamide, the mixture was stirred for 40 hours at room temperature. The mixture was poured into 200 ml of isopropyl ether and the mixture was stirred for 30 minutes and was then decanted. The gummy residue was triturated in 200 ml of isopropyl ether and then treated with 300 ml of ether. The mixture was stirred for 30 minutes and was vacuum filtered. The product was rinsed with ether and was then taken up in 30 ml of acetone. The solution was stirred for one hour and was vacuum filtered and the recovered product was rinsed with acetone, with ether and dried to obtain 1.243 g of the syn isomer of 2-(2 -tritylamino-4-thiazolyl)-2-(2-imidazol-1-yl-ethoxyimino)-acetic acid (internal imidazolium salt) melting at 280° C. (decomposition).

Workup

  1. stirringthe mixture was stirred for 40 hours at room temperature
  2. stirringthe mixture was stirred for 30 minutes
  3. customwas then decanted
  4. customThe gummy residue was triturated in 200 ml of isopropyl ether
  5. additiontreated with 300 ml of ether
  6. stirringThe mixture was stirred for 30 minutes
  7. filtrationfiltered
  8. washThe product was rinsed with ether
  9. stirringThe solution was stirred for one hour
  10. filtrationfiltered
  11. washthe recovered product was rinsed with acetone, with ether
  12. customdried

Sources & evidence

ORD record
ord-fbcadbaad3a941b286c52c731582ae20
Source dataset
uspto-grants-1984_03
Patent number
US04439433

Reaction notes

Loading…