Acetic Anhydride → HCID 53947050, compound

HRID 2379735Notes

Reaction equation

HRID 2379735 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([NH2:19])([CH2:15][CH2:16][CH2:17][CH3:18])[CH2:9][N:10]2[CH:14]=[N:13][CH:12]=[N:11]2)=[CH:4][CH:3]=1.[C:20](OC(=O)C)(=[O:22])[CH3:21]>C(Cl)Cl.C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([NH:19][C:20](=[O:22])[CH3:21])([CH2:15][CH2:16][CH2:17][CH3:18])[CH2:9][N:10]2[CH:14]=[N:13][CH:12]=[N:11]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 18956267HCID 18956267, compound

Product 1

HCID 53947050HCID 53947050, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred, cooled (0° C.) solution of 0.54 g (1.94 mmols) of [2-(4-chlorophenyl)-1-(1,2,4-triazol-1-yl)-2-hexylamine and 0.02 g (0.15 mmols) of N,N-dimethylaminopyridine in 10 mL of methylene chloride under nitrogen was added dropwise 0.50 mL (5.28 mmols) of acetic anhydride. After 5 days the reaction was quenched with the addition of methanol and the solvents were removed to give a white solid. The solid was dissolved in toluene which was removed under reduced pressure to remove any acetic acid. The resultant solid was recrystaltized from chloroform to give 0.2 g (32%) of white crystals, melting point 178.5°-179° C. 1H-NMR 200 MHz (CDCl3, Me4Si) 0.85 (t, J=7.5 Hz, CH2 -CH3), 1.0-1.4 (m, 4H), 1.8-2.2 (m, 2H), 2.05 (s, COCH3), 4.85 (ABq, J=35.3 Hz, JAB =12.5 Hz, CH2 -N), 5.95 (s, NH), 7.05-7.4 (q, aromatic H), 7.8 (s, CH=N), 7.95 ppm (s, CH=N).

Workup

  1. customAfter 5 days the reaction was quenched with the addition of methanol
  2. customthe solvents were removed
  3. customto give a white solid
  4. customwas removed under reduced pressure
  5. customto remove any acetic acid

Sources & evidence

ORD record
ord-a134e7bbbc304bf58fc198fddb869fe8
Source dataset
uspto-grants-1994_11
Patent number
US05364870

Reaction notes

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