Hydrochloric Acid → HCID 178463783, compound

HRID 1442459Notes

Reaction equation

HRID 1442459 reaction equation
S(O)(O)(=O)=O.[NH2:6][C:7]1[NH:8][CH:9]=[CH:10][N:11]=1.[NH2:12]C1NC=CN=1.Cl.[N+]([O-])([O-])=O.[Na+].[Br:24][CH2:25][CH2:26][N:27]([CH2:34][CH3:35])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(=O)(O)[O-].[Na+]>O.C(O)(=O)C>[Br:24][CH2:25][CH2:26][N:27]([CH2:34][CH3:35])[C:28]1[CH:33]=[CH:32][C:31](/[N:12]=[N:6]/[C:7]2[NH:8][CH:9]=[CH:10][N:11]=2)=[CH:30][CH:29]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 13228Aniline, N-(2-bromoethyl)-N-ethyl-HCID 24268Sodium NitrateHCID 516892Sodium BicarbonateHCID 27346842-Aminoimidazole hemisulfate

Product 1

HCID 178463783HCID 178463783, compoundYield 37.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

1.32 g 2-amino-1H-imidazol-hemisulfate is diazotized in a mixture containing 2 ml hydrochloric acid, 2 ml acetic acid, 12 ml water and 0.7 g sodium nitrate at 5° C. Azo coupling is performed by adding 2.3 g N-(2-bromoethyl)-N-ethylaniline to the above diazonium solution. After stirring for 2 hours at room temperature the mixture is poured on 50 ml saturated sodium bicarbonate. The resulted precipitate is filtered off, washed with water, and dried in vacuum at 40° C. After chromatography on silicagel with ethylacetate, 0.6 g N-(2-bromoethyl)-N-ethyl-4-[(E)-1H-imidazol-2-yldiazenyl]aniline is obtained as a brown powder.

Workup

  1. filtrationThe resulted precipitate is filtered off
  2. washwashed with water
  3. customdried in vacuum at 40° C

Sources & evidence

ORD record
ord-73821f5175fa490295e0a9bc96e6187a
Source dataset
uspto-grants-2010_02
Patent number
US07658770B2

Reaction notes

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