Triethylamine → HCID 21530408, compound

HRID 1657835Notes

Reaction equation

HRID 1657835 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH2:9])[C:5]([NH2:8])=[N:6][CH:7]=1.C(N(CC)CC)C.[F:17][C:18]([F:23])([F:22])[C:19](Cl)=[O:20]>O1CCCC1>[F:17][C:18]([F:23])([F:22])[C:19]([C:3]1[C:2]([Cl:1])=[CH:7][N:6]=[C:5]([NH2:8])[C:4]=1[NH2:9])=[O:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 61106Trifluoroacetyl chlorideHCID 12682545-Chloropyridine-2,3-diamine

Product 1

HCID 21530408HCID 21530408, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

5-Chloro-2,3-pyridinediamine (2.8 grams) was dissolved in 50 milliliters of tetrahydrofuran and 2.02 milliliters of triethylamine and the solution treated with trifluoroacetyl chloride (2.6 grams) in 100 milliliters of tetrahydrofuran. The addition was carried out at room temperature over a period of 2 hours, and the reaction mixture was then held at room temperature for another hour with stirring. Solvent was removed by evaporation, and the residue recrystallized from a chloroform/acetone mixture to obtain the desired N3 -trifluoroacetyl-5-chloro-2,3-pyridinediamine product, m.p., 292°-93°C.

Workup

  1. additionThe addition
  2. waitthe reaction mixture was then held at room temperature for another hour
  3. customSolvent was removed by evaporation
  4. customthe residue recrystallized from a chloroform/acetone mixture

Sources & evidence

ORD record
ord-4810b852449e4578b703c248439f0ef6
Source dataset
uspto-grants-1976_06
Patent number
US03962263

Reaction notes

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