Triethylamine → HCID 86596744, compound

HRID 2214915Notes

Reaction equation

HRID 2214915 reaction equation
N[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][N:3]=1.C([N:11](CC)CC)C.[CH3:16][C:17]([CH3:22])([CH3:21])[C:18](Cl)=[O:19]>C(Cl)Cl>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([CH2:16][C:17]([CH3:22])([CH3:21])[C:18]([NH2:11])=[O:19])=[N:3][CH:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 661742-Amino-5-chloropyridine

Product 1

HCID 86596744HCID 86596744, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 2-amino-5-chloropyridine (10.0 g, 0.078 mol) (Aldrich) and triethylamine (12 mL, 0.086 mol) in methylene chloride (200 mL), at 0° C., was added dropwise trimethylacetyl chloride in methylene chloride (15 mL). The reaction was allowed to warm to room temperature while stirring overnight. The resulting mixture was washed with water, brine, and was dried over MgSO4 and filtered. Concentration of the filtrate in vacuo provided a colorless oil (19.2 g). The oil was dissolved in hexanes and cooled causing the precipitation of a solid. The solid was collected by filtration affording the amide as a white solid (14.96 g, 90%): mp 51.4–53.4° C. 1H NMR (CDCl3/300 MHz) 8.25–8.15 (m, 2H), 8.00 (br s, 1H), 7.68–7.60 (m, 1H), 1.28 (s, 9H). Anal. Calc'd for C10H13N2OCl: C, 56.47; H, 6.16; N, 13.17 Found: C, 56.72; H, 6.34; N, 12.88.

Workup

  1. washThe resulting mixture was washed with water, brine
  2. dry with materialwas dried over MgSO4
  3. filtrationfiltered

Sources & evidence

ORD record
ord-c895be46ca4149b18d60b1763824263e
Source dataset
uspto-grants-2006_09
Patent number
US07109211B2

Reaction notes

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