Water → HCID 42603285, compound

HRID 2170543Notes

Reaction equation

HRID 2170543 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][N:10]2[C:14]([CH3:15])=[C:13]([C:16]([NH:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([CH2:25][OH:26])[CH:20]=3)=[O:17])[N:12]=[N:11]2)[CH:5]=[CH:6][C:7]=1[Cl:8].CCN(CC)CC.[C:34](Cl)(=[O:36])[CH3:35].O>C(Cl)Cl.C1COCC1>[C:34]([O:26][CH2:25][C:21]1[CH:22]=[CH:23][CH:24]=[C:19]([NH:18][C:16]([C:13]2[N:12]=[N:11][N:10]([CH2:9][C:4]3[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=3)[C:14]=2[CH3:15])=[O:17])[CH:20]=1)(=[O:36])[CH3:35]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 42603048HCID 42603048, compound

Product 1

HCID 42603285HCID 42603285, compound

Reagents, catalysts & solvents 1

HCID 21919333Tetrahydrofurane dichloromethaneSolvent

Procedure

To a solution of 1-[(3,4-dichlorophenyl)methyl]-N-[3-(hydroxymethyl)phenyl]-5-methyl-1H-1,2,3-triazole-4-carboxamide (Example 24) (0.1 g, 0.25 mmol) in a mixture of DCM/THF were added NEt3 (75 μL, 2 eq) and acetyl chloride (25 μL, 1.2 eq). The reaction was stirred at room temperature for 2 hours. Water was added and the product was extracted with ether, dried over sodium sulphate and evaporated in vacuo. The title compound was obtained as a white solid after recrystallisation from isopropyl ether (a couple drops of DCM) (60 mg, 54.5%). HRMS calculated for C20H18Cl2N4O3 (M+H)+433.0834. found: 433.0812, Rt: 3.14 min. MP: >70° C. (sticky).

Workup

  1. extractionthe product was extracted with ether
  2. dry with materialdried over sodium sulphate
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-964dee5f87324b18afb488af933645e2
Source dataset
uspto-grants-2015_06
Patent number
US09051281B2

Reaction notes

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