Triethylamine → HCID 20359940, compound

HRID 972939Notes

Reaction equation

HRID 972939 reaction equation
[Cl:1][C:2]1[C:3]([Br:17])=[C:4]2[N:11]([OH:12])[C:10]([C:13]([F:16])([F:15])[F:14])=[N:9][C:5]2=[N:6][C:7]=1[Br:8].[CH3:18][N:19]=[C:20]=[O:21].C(N(CC)CC)C>C(OCC)C>[CH3:18][NH:19][C:20]([O:12][N:11]1[C:4]2[C:5](=[N:6][C:7]([Br:8])=[C:2]([Cl:1])[C:3]=2[Br:17])[N:9]=[C:10]1[C:13]([F:14])([F:16])[F:15])=[O:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12228Methyl IsocyanateHCID 20355443HCID 20355443, compound

Product 1

HCID 20359940HCID 20359940, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

6-Chloro-5,7-dibromo-1-hydroxy-2-(trifluoromethyl)-1H-imidazo(4,5-b)pyridine (0.9 gram) was mixed with ether (15 milliliters) and methyl isocyanate (2 milliliters) and stirred for fifteen minutes. Triethylamine (0.01 milliliters) was added, and the solution became homogenous. It was permitted to stand for 16 hours, diluted with 50 milliliters diethyl ether; washed with 0.5NHC1, water, and saturated NaC1; then dried over magnesium sulfate, and evaporated. The resulting 1-(methylcarbamoyloxy)-6-chloro-5,7-dibromo-2-(trifluoromethyl)-1H-imidazo(4,5-b)pyridine product was recrystallized from chloroform, m.p., 216° C.

Workup

  1. washwashed with 0.5NHC1, water, and saturated NaC1
  2. dry with materialthen dried over magnesium sulfate
  3. customevaporated
  4. customThe resulting 1-(methylcarbamoyloxy)-6-chloro-5,7-dibromo-2-(trifluoromethyl)-1H-imidazo(4,5-b)pyridine product was recrystallized from chloroform
  5. customm.p., 216° C.

Sources & evidence

ORD record
ord-e9ed04166c28483dbb55c5bb99ddfc7b
Source dataset
uspto-grants-1977_10
Patent number
US04054573

Reaction notes

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