Water → 3,5-dibromo-1-trityl-1H-1,2,4-triazole

HRID 2105045Notes

Reaction equation

HRID 2105045 reaction equation
[C:1](Cl)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:21][C:22]1[N:26]=[C:25]([Br:27])[NH:24][N:23]=1.C(N(CC)CC)C.O>CN(C=O)C>[Br:21][C:22]1[N:26]=[C:25]([Br:27])[N:24]([C:1]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[N:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6456Trityl chlorideHCID 8471TriethylamineHCID 819043,5-Dibromo-4H-1,2,4-triazole

Product 1

HCID 578040363,5-dibromo-1-trityl-1H-1,2,4-triazoleYield 98.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Trityl chloride (6.8 g, 24 mmol) was added to a solution of 3,5-dibromo-1H-1,2,4-triazole (5 g, 22 mmol) and triethylamine (3.4 mL, 24.2 mmol) in DMF (100 mL) and stirred 16 h. The mixture was poured into rapidly stirred water (300 mL). The white precipitate was collected, washed with hexanes and dried on high vacuum to yield 10.2 g of Intermediate 359.1 as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 7.09-7.17 (m, 6H) 7.28-7.35 (m, 9H).

Workup

  1. customThe white precipitate was collected
  2. washwashed with hexanes
  3. customdried on high vacuum

Sources & evidence

ORD record
ord-5a2bd46f56a440dfb0392e5f85ce7480
Source dataset
uspto-grants-2009_08
Patent number
US07576098B2

Reaction notes

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