Trityl chloride → 5-(4'-Methyl[1,1'-biphenyl]-2-yl)-1-(triphenylmethyl)-1H-tetrazole

HRID 1656401Notes

Reaction equation

HRID 1656401 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:14]#[N:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1.C([Sn](Cl)(CCCC)CCCC)CCC.[N-:30]=[N+:31]=[N-:32].[Na+].[C:34](Cl)([C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>[OH-].[Na+].CCCCCCC.O.C1(C)C(C)=CC=CC=1>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]2[N:32]([C:34]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)([C:47]3[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=3)[C:41]3[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=3)[N:31]=[N:30][N:15]=2)=[CH:6][CH:7]=1

Participants

9

Reactant 4

HCID 6456Trityl chlorideHCID 15096Tributyltin ChlorideHCID 33557Sodium AzideHCID 1455122-Cyano-4'-methylbiphenyl

Product 1

HCID 101520195-(4'-Methyl[1,1'-biphenyl]-2-yl)-1-(triphenylmethyl)-1H-tetrazoleYield 80.7%

Reagents, catalysts & solvents 4

HCID 14798Sodium HydroxideCatalystHCID 962WaterSolventHCID 7237O-XyleneSolventHCID 8900HeptaneSolvent

Procedure

4'-Methylbiphenyl-2-nitrile (preparation described in European patent application 0253310, published on 20.01.88)(10.00 g, 51.7 mmol, 1 eq), tri-n-butyltin chloride (14.0 mL, 51.7 mmol, 1 eq), sodium azide (3.4 g 51.7 mmol, 1 eq), and xylene (50 mL) were mixed and refluxed for 64 h after which the reaction mixture was cooled to room temperature. 10.0N NaOH (6.10 mL, 0.061 mmol, 1.2 eq) and trityl chloride (14.99 g, 53.8 mmol, 1.04 eq) were then added and the mixture stirred for 24 h after which water (39 mL) and heptane (100 mL) were added. The resultant slurry was stirred at 0° C. for 1.5 h. The resultant solids thus obtained were filtered, washed with water (2×55 mL) washed once with 3:2 heptane/toluene (55 mL) and dried overnight under high vacuum to yield 19.97 g of a light yellow powder; mp 148.0°-155.0° C. (dec.). These solids were slurried in ethyl acetate (75 mL) and filtered to yield 15.0 g of a light yellow powder: mp 164.0°-165.5° C. (dec.). NMR (CDCl3) δ 7.91 (d, 1H, J=9 Hz); 7.53-7.18 (m, 13H); 7.02-6.84 (m, 9H); 2.25 (s, 3H). ##STR76##

Workup

  1. temperaturerefluxed for 64 h after which the reaction mixture
  2. additionwere added
  3. customThe resultant solids thus obtained
  4. filtrationwere filtered
  5. washwashed with water (2×55 mL)
  6. washwashed once with 3:2 heptane/toluene (55 mL)
  7. customdried overnight under high vacuum

Sources & evidence

ORD record
ord-13b3d584785a4a4099899f8b23235ce9
Source dataset
uspto-grants-1993_10
Patent number
US05254546

Reaction notes

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