1,1'-Carbonyldiimidazole → 2-(4-benzyloxyphenoxy)-N-[3-(imidazol-1-yl)propyl]acetamide

HRID 378598Notes

Reaction equation

HRID 378598 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:13]([O:20][C:21]1[CH:31]=[CH:30][C:24]([O:25][CH2:26][C:27]([OH:29])=O)=[CH:23][CH:22]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[NH2:32][CH2:33][CH2:34][CH2:35][N:36]1[CH:40]=[CH:39][N:38]=[CH:37]1>C1COCC1>[CH2:13]([O:20][C:21]1[CH:22]=[CH:23][C:24]([O:25][CH2:26][C:27]([NH:32][CH2:33][CH2:34][CH2:35][N:36]2[CH:40]=[CH:39][N:38]=[CH:37]2)=[O:29])=[CH:30][CH:31]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 787361H-Imidazole-1-propanamineHCID 563696(4-(Phenylmethoxy)phenoxy)acetic acid

Product 1

HCID 220074712-(4-benzyloxyphenoxy)-N-[3-(imidazol-1-yl)propyl]acetamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1,1'-Carbonyldiimidazole (16.2 g) was added to a stirred suspension of 4-benzyloxyphenoxyacetic acid (25.8 g) in dry THF (350 ml) and the mixture was stirred at ambient temperature for 2 hours. 1-(3-Aminopropyl)imidazole (12.5 g) was added and the mixture was stirred for a further 18 hours. The mixture was filtered and the filtrate evaporated to give a residue which was treated as in Example 9a to give 2-(4-benzyloxyphenoxy)-N-[3-(imidazol-1-yl)propyl]acetamide m.p. 112-113° C.

Workup

  1. stirringthe mixture was stirred for a further 18 hours
  2. filtrationThe mixture was filtered
  3. customthe filtrate evaporated
  4. customto give a residue which
  5. additionwas treated as in Example 9a

Sources & evidence

ORD record
ord-53d9b24a29214348860ac07d8e57e81e
Source dataset
uspto-grants-2000_02
Patent number
US06031109

Reaction notes

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