1-Bromomethyl-2,6-dichlorobenzene → 5-(4-Chlorophenyl)-4-cyclopropyl-2-{[1-(2,6-dichlorobenzyl)-1H-1,2,4-triazol-5-yl]sulfonyl}-2,4-dihydro-3H-1,2,4-triazol-3-one

HRID 714722Notes

Reaction equation

HRID 714722 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH:22]3[CH2:24][CH2:23]3)[C:10](=[O:21])[N:11]([S:13]([C:16]3[NH:20][N:19]=[CH:18][N:17]=3)(=[O:15])=[O:14])[N:12]=2)=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.[Cl:34][C:35]1[CH:42]=[CH:41][CH:40]=[C:39]([Cl:43])[C:36]=1[CH2:37]Br>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]([CH:22]3[CH2:24][CH2:23]3)[C:10](=[O:21])[N:11]([S:13]([C:16]3[N:20]([CH2:37][C:36]4[C:35]([Cl:34])=[CH:42][CH:41]=[CH:40][C:39]=4[Cl:43])[N:19]=[CH:18][N:17]=3)(=[O:15])=[O:14])[N:12]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 301591-Bromomethyl-2,6-dichlorobenzeneHCID 81531DiisopropylethylamineHCID 699405625-(4-Chlorophenyl)-4-cyclopropyl-2-(1H-1,2,4-triazol-5-ylsulfonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one

Product 1

HCID 673952085-(4-Chlorophenyl)-4-cyclopropyl-2-{[1-(2,6-dichlorobenzyl)-1H-1,2,4-triazol-5-yl]sulfonyl}-2,4-dihydro-3H-1,2,4-triazol-3-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

37 mg (0.10 mmol) of the compound from Example 93A were dissolved in 3 ml of dichloromethane, and 21 μl (0.13 mmol) of N,N-diisopropylethylamine were added. 30 mg (0.13 mmol) of 2,6-dichlorobenzyl bromide dissolved in 1 ml of dichloromethane were then added, and the mixture was stirred at RT for 20 h. For work-up, the mixture was concentrated under reduced pressure and the crude product was purified chromatographically [Method 19]. This gave 39 mg (74% of theory) of the target compound.

Workup

  1. additionwere then added
  2. concentrationFor work-up, the mixture was concentrated under reduced pressure
  3. customthe crude product was purified chromatographically [Method 19]

Sources & evidence

ORD record
ord-2bc4e630fa8641109d14a432f2c07116
Source dataset
uspto-grants-2015_11
Patent number
US09187466B2

Reaction notes

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