Sodium Azide → 1-(2-azidoethyl)-1H-benzimidazole-5-carboxylic acid methyl ester

HRID 555292Notes

Reaction equation

HRID 555292 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:16]=[CH:15][C:8]2[N:9]([CH2:12][CH2:13]Cl)[CH:10]=[N:11][C:7]=2[CH:6]=1)=[O:4].[N-:17]=[N+:18]=[N-:19].[Na+]>CS(C)=O>[CH3:1][O:2][C:3]([C:5]1[CH:16]=[CH:15][C:8]2[N:9]([CH2:12][CH2:13][N:17]=[N+:18]=[N-:19])[CH:10]=[N:11][C:7]=2[CH:6]=1)=[O:4]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 669873921-(2-chloroethyl)-1H-benzimidazole-5-carboxylic acid methyl ester

Product 1

HCID 866300571-(2-azidoethyl)-1H-benzimidazole-5-carboxylic acid methyl esterYield 91.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of 1-(2-chloroethyl)-1H-benzimidazole-5-carboxylic acid methyl ester (9.9 g, 0.0416 mol) in dry DMSO (90 mL) was added with stirring NaN3 (5.4 g, 0.0832 mol) and the mixture was stirred for 15 h at 75° C. The reaction mixture was cooled to ambient temperature and diluted with ice water (500 mL) and the solid precipitated was filtered, washed with water and dried under vacuum affording 9.3 g (91%) of 1-(2-azidoethyl)-1H-benzimidazole-5-carboxylic acid methyl ester as a solid. MS-ESI m/z 246 (M+1); 1H NMR (300 MHz, DMSO-d6) δ 3.8 (t, 2H), 3.9 (s, 3H), 4.5 (t, 2H), 7.8 (d, 1H), 7.9 (dd, 1H), 8.25 (s, 1H), 8.4 (s, 1H).

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. customthe solid precipitated
  3. filtrationwas filtered
  4. washwashed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-db11c707dc5644f98c5c098427a6649a
Source dataset
uspto-grants-2011_11
Patent number
US08053431B2

Reaction notes

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