Triethylamine → N-(2-propynyl)-2-naphthalenecarboxamide

HRID 2225740Notes

Reaction equation

HRID 2225740 reaction equation
[CH2:1]([NH2:4])[C:2]#[CH:3].C(N(CC)CC)C.[CH:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][C:13]=1[C:22](Cl)=[O:23]>ClCCl.C(OCC)(=O)C>[CH2:1]([NH:4][C:22]([C:13]1[CH:14]=[CH:15][C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:12]=1)=[O:23])[C:2]#[CH:3]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 752462-Naphthoyl chlorideHCID 239041Propargylamine

Product 1

HCID 16375226N-(2-propynyl)-2-naphthalenecarboxamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Propargylamine (0.80 mL) and triethylamine (1.67 mL) were added simultaneously to a solution of 2-naphthoyl chloride (2.22 g) in dichloromethane (25 mL) cooled in an ice bath. The mixture was held at 0° C. for 1 hour and allowed to warm to room temperature over 3 hours. The solution was diluted with ethyl acetate, washed in turn with water, 1N hydrochloric acid, 1N sodium hydroxide, and saturated brine. Evaporation of the dried (K2CO3) organic layer gave a residue which was crystallized from dichloromethanehexane to give 2.06 g of N-(2-propynyl)-2-naphthalenecarboxamide, mp 163°-165° C.

Workup

  1. temperaturecooled in an ice bath
  2. washwashed in turn with water, 1N hydrochloric acid, 1N sodium hydroxide, and saturated brine
  3. customEvaporation of the
  4. dry with materialdried (K2CO3) organic layer
  5. customgave a residue which
  6. customwas crystallized from dichloromethanehexane

Sources & evidence

ORD record
ord-e6e2e76053974e138a6fe88b47138da6
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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