Water → HCID 178463665, compound

HRID 1455941Notes

Reaction equation

HRID 1455941 reaction equation
[CH2:1]([O:8][C:9]1[CH:26]=[CH:25][C:24]([Br:27])=[CH:23][C:10]=1[CH2:11][N:12]([C:15]1[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][CH:16]=1)[CH2:13][CH3:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:28]=[N+:29]=[N-:30].[Na+].[Cl-].[NH4+].O>CN(C)C=O>[CH2:1]([O:8][C:9]1[CH:26]=[CH:25][C:24]([Br:27])=[CH:23][C:10]=1[CH2:11][N:12]([C:15]1[CH:16]=[CH:17][C:18]([C:19]2[NH:30][N:29]=[N:28][N:20]=2)=[CH:21][CH:22]=1)[CH2:13][CH3:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 22105536HCID 22105536, compound

Product 1

HCID 178463665HCID 178463665, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 4-[N-(2-benzyloxy-5-bromobenzyl)-N-ethyl-amino]benzonitrile (3.79 g), sodium azide (0.9 g) and ammonium chloride (1.4 g) in N,N-dimethylformamide (30 mL) was heated and stirred at 120° C. for 18 hours. The reaction mixture was allowed to cool and was poured into water (100 mL). The precipitate was filtered and dried. On crystallization from acetic acid there was obtained 5-[4-[N-(2- benzyloxy-5-bromobenzyl)-N-ethylamino)phenyl]tetrazole, yield 1.2 g, mp 206°-208° C.

Workup

  1. temperaturewas heated
  2. temperatureto cool
  3. filtrationThe precipitate was filtered
  4. customdried
  5. customOn crystallization from acetic acid

Sources & evidence

ORD record
ord-208c6010d7e7408f92880f72420fe13b
Source dataset
uspto-grants-1998_12
Patent number
US05843942

Reaction notes

Loading…