Hydrochloric Acid → HCID 20355443, compound

HRID 371664Notes

Reaction equation

HRID 371664 reaction equation
[Br:1][C:2]1[N:7]=[C:6]2[N:8]=[C:9]([C:12]([F:15])([F:14])[F:13])[N:10]([OH:11])[C:5]2=[C:4]([Br:16])[C:3]=1N.N([O-])=O.[Na+].[ClH:22]>>[Br:1][C:2]1[N:7]=[C:6]2[N:8]=[C:9]([C:12]([F:15])([F:14])[F:13])[N:10]([OH:11])[C:5]2=[C:4]([Br:16])[C:3]=1[Cl:22]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 20355447HCID 20355447, compoundHCID 23668193Sodium Nitrite2×

Product 1

HCID 20355443HCID 20355443, compound

Procedure

5,7-Dibromo-6-amino-1-hydroxy-2-(trifluoromethyl)-1H-imidazo(4,5-b)pyridine (1.2 grams) in 7 milliliters of concentrated HCl was cooled to 0°-10° C. Thereafter, sodium nitrite (0.35 gram) was added as a solid. The addition was carried out portionwise to maintain the temperature below 10° C. Five minutes after completion of the addition of the sodium nitrite, cuprous chloride (0.45 gram) was added portionwise and the resulting reaction mixture stirred for thirty minutes and filtered to separate the desired 5,7-dibromo-6-chloro-1-hydroxy-2-(trifluoromethyl)-1H-imidazo(4,5-b)pyridine product, m.p., 215° C.

Workup

  1. additionThe addition
  2. temperatureto maintain the temperature below 10° C
  3. additionwas added portionwise
  4. customthe resulting reaction mixture
  5. filtrationfiltered
  6. customto separate the desired 5,7-dibromo-6-chloro-1-hydroxy-2-(trifluoromethyl)-1H-imidazo(4,5-b)pyridine product
  7. customm.p., 215° C.

Sources & evidence

ORD record
ord-e5cb47df72df435a98b190da391fdbf1
Source dataset
uspto-grants-1978_05
Patent number
US04087432

Reaction notes

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