Trimethyl orthoacetate → HCID 14232984, compound

HRID 580475Notes

Reaction equation

HRID 580475 reaction equation
[NH2:1][C:2]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:3]=1[C:4]([NH:6][CH2:7][CH2:8][CH2:9][N:10]1[CH:14]=[CH:13][N:12]=[CH:11]1)=[O:5].[C:20](OC)(OC)(OC)[CH3:21]>C(O)C>[Cl:19][C:16]1[CH:15]=[C:3]2[C:2](=[CH:18][CH:17]=1)[N:1]=[C:20]([CH3:21])[N:6]([CH2:7][CH2:8][CH2:9][N:10]1[CH:14]=[CH:13][N:12]=[CH:11]1)[C:4]2=[O:5]

Participants

4

Reactant 2

HCID 15050Trimethyl orthoacetateHCID 135889602-Amino-5-chloro-N-[3-(1H-imidazol-1-yl)propyl]benzamide

Product 1

HCID 14232984HCID 14232984, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2.79 g of 2-amino-5-chloro-N-[3-(1H-imidazol-1-yl)propyl]benzamide, 5 ml of trimethyl orthoacetate and 10 ml of ethyl alcohol was heated at reflux for 24 hours. The resulting solution was concentrated and the residue was triturated with ether and gave a solid. The ether was decanted and the solid was dissolved in ethyl acetate and allowed to stand. The precipitate was collected and gave 650 mg of the desired product as tan crystals, mp 190°-192° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 24 hours
  3. concentrationThe resulting solution was concentrated
  4. customthe residue was triturated with ether
  5. customgave a solid
  6. customThe ether was decanted
  7. dissolutionthe solid was dissolved in ethyl acetate
  8. customThe precipitate was collected

Sources & evidence

ORD record
ord-76e94dc9143d4c568ba86cd50c6e953a
Source dataset
uspto-grants-1988_06
Patent number
US04753944

Reaction notes

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