Acetic Anhydride → HCID 15096587, compound

HRID 2107640Notes

Reaction equation

HRID 2107640 reaction equation
[Cl:1][C:2]([Cl:20])([Cl:19])[CH2:3][C:4]([C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)([OH:11])[CH2:5][N:6]1[CH:10]=[N:9][CH:8]=[N:7]1.[C:21](OC(=O)C)(=[O:23])[CH3:22]>C1C=CC=CC=1.CN(C)C1C=CN=CC=1>[C:21]([O:11][C:4]([C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)([CH2:5][N:6]1[CH:10]=[N:9][CH:8]=[N:7]1)[CH2:3][C:2]([Cl:19])([Cl:1])[Cl:20])(=[O:23])[CH3:22]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 15096576HCID 15096576, compound

Product 1

HCID 15096587HCID 15096587, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 241BenzeneSolvent2×

Procedure

Five (5) g (0.0141 mol) of 4,4,4-trichloro-2-(4-chlorophenyl)-2-hydroxy-(1,2,4-(1H)-triazolyl)butane (prepared as in Example I) was slurried in 75 mls of benzene, 4.31 g (0.0422 mol) of acetic anhydride and 2.6 g (0.0211 mol) of 4-dimethylaminopyridine. This mixture was stirred at room temperature for 30 hours and then diluted with 75 mls of benzene. The mixture was washed thrice with 100 mL portions of water. Evaporation of the solvent under reduced pressure and purification of the residue by preparative high pressure liquid chromatography (HPLC) in a 1:1 mixture of ethyl acetate and hexane gave the desired product as a white solid in a yield of 2.2 g (39 percent of theoretical) melting at 112°-114° C.

Workup

  1. washThe mixture was washed thrice with 100 mL portions of water
  2. customEvaporation of the solvent
  3. customunder reduced pressure and purification of the residue by preparative high pressure liquid chromatography (HPLC)
  4. additionin a 1:1 mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-826ae586cba3441c883bc00cd0b677e4
Source dataset
uspto-grants-1990_06
Patent number
US04935436

Reaction notes

Loading…