Benzoyl Peroxide → HCID 66938894, compound

HRID 1176092Notes

Reaction equation

HRID 1176092 reaction equation
N([CH2:4][C:5]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:6]=1[C:12]1[N:16]([C:17]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:15]=[N:14][N:13]=1)=[N+]=[N-].C1C(=O)N([Br:43])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)Cl>[Br:43][CH2:4][C:5]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:6]=1[C:12]1[N:16]([C:17]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:15]=[N:14][N:13]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimide2×HCID 86621227HCID 86621227, compound

Product 1

HCID 66938894HCID 66938894, compoundYield 74.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

5-(2-Azidomethyl-4-chloro-phenyl)-1-trityl-1H-tetrazole: To 114A (4 g, 9.15 mmol) in chloroform (20 mL) was added NBS (1.711 g, 9.61 mmol) and benzoyl peroxide (30 mg, 0.124 mmol) and the reaction was heated at reflux overnight. Additional NBS and peroxide were added and the reaction was heated an addition 2 h. The reaction was cooled to rt, filtered, and purified by flash chromatography to give 5-(2-bromomethyl-4-chloro-phenyl)-1-trityl-1H-tetrazole (3.5 g, 74.1%). 1HNMR (400 MHz, CDCl3) δ: 4.78 (s, 2 H), 7.04-7.14 (m, 5 H), 7.24-7.35 (m, 11 H), 7.40 (d, J=2.02 Hz, 1 H), 8.06 (d, J=8.34 Hz, 1 H). This intermediate (1.57 g, 3.04 mmol) and sodium azide (0.198 g, 3.04 mmol) in DMF (8 mL) were stirred for two days. The reaction was partitioned with EtOAc/water/brine and extracted with EtOAc. The combined organic layers were washed with water and brine, dried (MgSO4), and purified by flash chromatography to give 114B. LCMS m/z 195.2 (M+H—N3)+; 152.1 (M+H—N6).

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux overnight
  3. temperaturethe reaction was heated
  4. additionan addition 2 h
  5. filtrationfiltered
  6. custompurified by flash chromatography

Sources & evidence

ORD record
ord-d5cf68e40b6140d797be9d3a4b75f092
Source dataset
uspto-grants-2010_11
Patent number
US07842708B2

Reaction notes

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