Triethylamine → HCID 19892772, compound

HRID 893077Notes

Reaction equation

HRID 893077 reaction equation
[Br:1]C(Cl)(Cl)C(Cl)(Cl)Br.C(N(CC)CC)C.[F:16][C:17]1[CH:22]=[CH:21][C:20]([NH:23][C:24]([CH:26]2[CH2:28][CH2:27]2)=O)=[CH:19][N:18]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCCl>[F:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]=[C:24]([Br:1])[CH:26]2[CH2:28][CH2:27]2)=[CH:19][N:18]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 694261,2-Dibromo-1,1,2,2-tetrachloroethaneHCID 14304481N-(6-Fluoro-3-pyridinyl)cyclopropanecarboxamide

Product 1

HCID 19892772HCID 19892772, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

A solution of 1,2-dibromotetrachloroethane (7.23 g, 0.022 mol) in 1,2-dichloroethane (50 ml) and triethylamine (4.49 g, 0.044 mol) was added to a stirred suspension of N-(2-fluoro-5-pyridyl)-cyclopropane carboxamide (2.0 g, 0.011 mol) - see Example 2 stage 1 and triphenylphosphine (5.83 g, 0.022 mol) in 1,2-dichloroethane (25 ml) at -10° C. under nitrogen at such a rate so that the temperature did not rise above -10° C. After complete addition (11/4 hours) the reaction mixture was allowed to warm up to room temperature and any triphenyl phosphine oxide was removed by filtration. Further quantities of triphenylphosphine oxide were removed by trituration of the residue with hexane. The filtrate was evaporated to give N-(2-fluoro-5-pyridyl)-cyclopropylmethanimidoyl bromide (2.54 g, 95%) as a yellow crystalline solid which was used in the next stage without further purification or characterisation.

Workup

  1. customdid not rise above -10° C
  2. additionAfter complete addition (11/4 hours) the reaction mixture
  3. customany triphenyl phosphine oxide was removed by filtration
  4. customFurther quantities of triphenylphosphine oxide were removed by trituration of the residue with hexane
  5. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-e704b1a452484a21865a54970980e9d6
Source dataset
uspto-grants-1992_06
Patent number
US05122529

Reaction notes

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