Tert-Butyl hypochlorite → HCID 46198850, compound

HRID 2061041Notes

Reaction equation

HRID 2061041 reaction equation
[ClH:1].[NH2:2][C:3]([C:6]1[N:7]=[N:8][N:9]([CH2:11][CH2:12][N+:13]([CH3:16])([CH3:15])[CH3:14])[CH:10]=1)([CH3:5])[CH3:4].[Cl:17]OC(C)(C)C>CO>[Cl-:17].[Cl:1][N:2]([Cl:17])[C:3]([C:6]1[N:7]=[N:8][N:9]([CH2:11][CH2:12][N+:13]([CH3:14])([CH3:16])[CH3:15])[CH:10]=1)([CH3:5])[CH3:4]

Participants

4

Reactant 2

HCID 521297Tert-Butyl hypochloriteHCID 67318639HCID 67318639, compound

Product 1

HCID 46198850HCID 46198850, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-(4-(2-aminopropan-2-yl)-1H-1,2,3-triazol-1-yl)-N,N,N-trimethylethanaminium hydrochloride (1.45 g, 5.8 mmol) in methanol (100 ml) was stirred at room temperature. t-Butyl hypochlorite (1.90 g, 17.5 mmol) was added to the mixture, and the combined mixture was stirred for 1 hour at room temperature. The reaction mixture was concentrated in vacuo, and purified by prep-HPLC to give 769 mg (42% yield) of 2-(4-(2-(dichloroamino)propan-2-yl)-1H-1,2,3-triazol-1-yl)-N,N,N-trimethylethanaminium chloride. 1H NMR (D2O) δ 8.41 (s, 1 H), 5.10 (t, J=4.7, 2 H), 4.06 (t, J=4.7, 2 H), 3.18 (s, 9 H), 1.83 (s, 6H); MS (ESI+) calculated for C10H20Cl2N5+: 280.11. Found: 280.1 (M+).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompurified by prep-HPLC

Sources & evidence

ORD record
ord-7ce6e227ed5147edb069f68f92a66051
Source dataset
uspto-grants-2012_10
Patent number
US08278482B2

Reaction notes

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