Anthracene-9-carbonyl chloride → N-(Prop-2-YN-1-YL)anthracene-9-carboxamide

HRID 1678895Notes

Reaction equation

HRID 1678895 reaction equation
[CH:1]1[C:14]2[C:5](=[CH:6][C:7]3[C:12]([C:13]=2[C:15](Cl)=[O:16])=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1.[CH2:18]([NH2:21])[C:19]#[CH:20]>O1CCCC1>[CH2:18]([NH:21][C:15]([C:13]1[C:14]2[C:5]([CH:6]=[C:7]3[C:12]=1[CH:11]=[CH:10][CH:9]=[CH:8]3)=[CH:4][CH:3]=[CH:2][CH:1]=2)=[O:16])[C:19]#[CH:20]

Participants

4

Reactant 2

HCID 167528Anthracene-9-carbonyl chlorideHCID 239041Propargylamine

Product 1

HCID 12623565N-(Prop-2-YN-1-YL)anthracene-9-carboxamideYield 98.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 13.68 g of 9-anthroyl chloride in 30 ml of tetrahydrofuran is added at 10°-15° to a solution of 10 g of propargylamine in 60 ml of tetrahydrofuran. After stirring at room temperature for 4 hours, the solvent is removed and the residue is stirred with methylene chloride and 5% aqueous sodium bicarbonate solution. The methylene chloride layer is dried and concentrated to give 14.54 g of crude N-propargyl-9-anthramide as a solid. An analytical sample (ethanol) had a melting point of 201°-202°; H nmr spectrum: τ 1.5-2.8 (m, 9); 3.7 (broad, 1); 5.7 (d of d, 2) and 7.7 (τ, 2.5 Hz, 1).

Workup

  1. customthe solvent is removed
  2. stirringthe residue is stirred with methylene chloride and 5% aqueous sodium bicarbonate solution
  3. dry with materialThe methylene chloride layer is dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0e2629eee43f4e70897f186719ac5b71
Source dataset
uspto-grants-1978_03
Patent number
US04077977

Reaction notes

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