Acetic Anhydride → HCID 20068379, compound

HRID 1638260Notes

Reaction equation

HRID 1638260 reaction equation
[CH3:1][C:2]1([CH3:19])[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]1[N:12]1[C:16]([CH2:17][NH2:18])=[CH:15][N:14]=[CH:13]1.[C:20](OC(=O)C)(=[O:22])[CH3:21]>ClC(Cl)Cl>[CH3:1][C:2]1([CH3:19])[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]1[N:12]1[C:16]([CH2:17][NH:18][C:20](=[O:22])[CH3:21])=[CH:15][N:14]=[CH:13]1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 20068400HCID 20068400, compound

Product 1

HCID 20068379HCID 20068379, compoundYield 60.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a stirred mixture of 5.1 parts of 1-(1,2,3,4-tetrahydro-2,2-dimethyl-1-naphthalenyl)-1H-imidazole-5-methanamine and 75 parts of trichloromethane was added dropwise a solution of 2.0 parts of acetic acid anhydride in 150 parts of trichloromethane. Upon complete addition, stirring was continued for 1 hour at room temperature. The reaction mixture was washed with a sodium carbonate solution 10% and water, dried, filtered and evaporated. The residue was crystallized from 2-propanone. The product was filtered off and dried, yielding 3.61 parts (60.6%) of N-[[1-(1,2,3,4-tetrahydro-2,2-dimethyl-1-naphthalenyl)-1H-imidazol-5-yl]methyl]acetamide; mp. 166.3° C. (compound 2.47).

Workup

  1. additionUpon complete addition
  2. washThe reaction mixture was washed with a sodium carbonate solution 10% and water
  3. customdried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was crystallized from 2-propanone
  7. filtrationThe product was filtered off
  8. customdried

Sources & evidence

ORD record
ord-bbf3acb2984649ea91e517861f162bd5
Source dataset
uspto-grants-1989_11
Patent number
US04878940

Reaction notes

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