Azido(trimethyl)stannane → 1-[(2'-(Trimethylstannyltetrazol-5-yl)biphenyl-4-yl)methyl]-2-butyl-4-chloro-5-hydroxymethylimidazole

HRID 653937Notes

Reaction equation

HRID 653937 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][N:16]2[C:20]([CH2:21][OH:22])=[C:19]([Cl:23])[N:18]=[C:17]2[CH2:24][CH2:25][CH2:26][CH3:27])=[CH:11][CH:10]=1)#[N:2].[CH3:28][Sn:29]([N:32]=[N+:33]=[N-:34])([CH3:31])[CH3:30]>>[CH3:28][Sn:29]([N:32]1[C:1]([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[C:9]2[CH:10]=[CH:11][C:12]([CH2:15][N:16]3[C:20]([CH2:21][OH:22])=[C:19]([Cl:23])[N:18]=[C:17]3[CH2:24][CH2:25][CH2:26][CH3:27])=[CH:13][CH:14]=2)=[N:2][N:34]=[N:33]1)([CH3:31])[CH3:30]

Participants

3

Reactant 2

HCID 5104973Azido(trimethyl)stannaneHCID 144256644'-((2-Butyl-4-chloro-5-(hydroxymethyl)-1H-imidazol-1-yl)methyl)(1,1'-biphenyl)-2-carbonitrile

Product 1

HCID 144256651-[(2'-(Trimethylstannyltetrazol-5-yl)biphenyl-4-yl)methyl]-2-butyl-4-chloro-5-hydroxymethylimidazole

Conditions

Temperature
115 °C

Procedure

1-[(2'-Cyanobiphenyl-4-yl)methyl]-2-butyl-4-chloro-5-hydroxymethylimidazole (766 g), trimethyl tin azide (766 g) and xylenes (7.90 L) were charged to a 12 liter round-bottomed flask equipped with mechanical stirrer, condenser with N2 inlet and thermometer contained in a heating mantle. The slurry was heated to 115° C., giving a clear solution, and held for 41 hours. The resulting slurry was cooled to room temperature and the crude product isolated by vacuum filtration, washed with toluene (800 ml) and dried in vacuo at ~50° C. overnight. The crude product (1202 g) was charged to a 12 liter round-bottomed flask and slurried at 105° C. with toluene (70 L). The slurry was cooled to 50° C. and the product isolated by vacuum filtration, washed with one liter of toluene and dried in vacuo at 50° C. overnight. Yield: 1071 g, 94%. M.P.: 211°-214° C.

Workup

  1. customequipped with mechanical stirrer, condenser with N2 inlet
  2. customgiving a clear solution
  3. temperatureThe resulting slurry was cooled to room temperature

Sources & evidence

ORD record
ord-e1f8641f97a44acfb2bb54c1e497e673
Source dataset
uspto-grants-1992_07
Patent number
US05128355

Reaction notes

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