Triethylamine → Hydrochloric Acid

HRID 1659851Notes

Reaction equation

HRID 1659851 reaction equation
[CH3:1][CH:2]1[CH2:7][NH:6][CH2:5][CH2:4][N:3]1[CH2:8][CH2:9][CH2:10][CH2:11][N:12]1[C:21](=[O:22])[CH2:20][C:15]2([CH2:19][CH2:18][CH2:17][CH2:16]2)[CH2:14][C:13]1=[O:23].[Cl:24][C:25]1[C:30]([C:31]#[N:32])=[CH:29][CH:28]=[CH:27][N:26]=1.C(N(CC)CC)C>C(O)C>[O:23]=[C:13]1[N:12]([CH2:11][CH2:10][CH2:9][CH2:8][N:3]2[CH2:4][CH2:5][N:6]([C:25]3[C:30]([C:31]#[N:32])=[CH:29][CH:28]=[CH:27][N:26]=3)[CH2:7][CH:2]2[CH3:1])[C:21](=[O:22])[CH2:20][C:15]2([CH2:16][CH2:17][CH2:18][CH2:19]2)[CH2:14]1.[ClH:24]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 810792-ChloronicotinonitrileHCID 12790502HCID 12790502, compound

Product 2

HCID 313Hydrochloric AcidHCID 20558633HCID 20558633, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The product of Procedure 4, 3.38 g. (0.0105 mole) was caused to react with 1.46 g. (0.0105 mole) of 2-chloro-3-cyanopyridine in the presence of 1.06 g. (0.0105 mole) of triethylamine in 40 ml. of ethanol in a pressure vessel as described in Procedure 2. The crude product, 3.58 g., was recovered as an oil which was dissolved in 30 ml. of ethanol and treated with 2 molecular proportions of ethanolic hydrogen chloride. The solvent was removed by distillation, and the residue was dried by azeotropic distillation with benzene which resulted in crystallization of the desired product as the monohydrochloride, m.p. 181°-183°.

Workup

  1. customto react with 1.46 g
  2. custom, was recovered as an oil which
  3. dissolutionwas dissolved in 30 ml
  4. additionof ethanol and treated with 2 molecular proportions of ethanolic hydrogen chloride
  5. customThe solvent was removed by distillation
  6. dry with materialthe residue was dried by azeotropic distillation with benzene which

Sources & evidence

ORD record
ord-76a36f28c22b4b92aed1d820139f3c67
Source dataset
uspto-grants-1981_12
Patent number
US04305944

Reaction notes

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