Triethylamine → N-(3-methylpent-1-yn-3-yl)-4-nitrobenzamide

HRID 583134

Reaction equation

HRID 583134 reaction equation
Cl.[NH2:2][C:3]([CH3:8])([CH2:6][CH3:7])[C:4]#[CH:5].C(N(CC)CC)C.[N+:16]([C:19]1[CH:27]=[CH:26][C:22]([C:23](Cl)=[O:24])=[CH:21][CH:20]=1)([O-:18])=[O:17]>C(Cl)Cl>[CH3:8][C:3]([NH:2][C:23](=[O:24])[C:22]1[CH:21]=[CH:20][C:19]([N+:16]([O-:18])=[O:17])=[CH:27][CH:26]=1)([CH2:6][CH3:7])[C:4]#[CH:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 85024-Nitrobenzoyl chlorideHCID 122329903-Methyl-1-pentyn-3-amine hydrochloride2×

Product 1

HCID 15405291N-(3-methylpent-1-yn-3-yl)-4-nitrobenzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a three-necked, round-bottomed flask fitted with a mechanical stirrer, nitrogen inlet and thermometer were placed 4 grams (g) (0.03 mole) of 3-amino-3-methyl-1-pentyne hydrochloride (4 grams (g) (0.03 mole) suspended in 100 milliliters (mL) of methylene chloride in a three-necked, round-bottomed flask fitted with a mechanical stirrer, nitrogen inlet and thermometer. Triethylamine (6.82 g, 9.4 mL) was added slowly, keeping the temperature between 5° C. and 10° C. 4-nitrobenzoyl chloride 5 g (0.027 mole) was added to the resulting mixture at a rate to keep the reaction temperature between 5° C. and 10° C. After the addition was complete the reaction mixture was stirred at room temperature for 0.5 hours, and was then sequentially washed with water (2×100 mL), 5% aqueous hydrochloric acid, (2×100 mL), water (1×50 mL), 5% aqueous sodium hydroxide (2×100 mL) and finally with water (1×100 mL) before being dried over anhydrous magnesium sulfate. The solvent was removed in the rotary evaporator, yielding N-(3-methylpent-1-yn-3-yl)-4-nitrobenzamide, used as such in the next step.

Workup

  1. customIn a three-necked, round-bottomed flask fitted with a mechanical stirrer, nitrogen inlet
  2. customfitted with a mechanical stirrer, nitrogen inlet
  3. customthe temperature between 5° C. and 10° C
  4. customthe reaction temperature between 5° C. and 10° C
  5. additionAfter the addition
  6. washwas then sequentially washed with water (2×100 mL), 5% aqueous hydrochloric acid, (2×100 mL), water (1×50 mL), 5% aqueous sodium hydroxide (2×100 mL) and finally with water (1×100 mL)
  7. dry with materialbefore being dried over anhydrous magnesium sulfate
  8. customThe solvent was removed in the rotary evaporator

Sources & evidence

ORD record
ord-3462e37789814c90a554d3fd75a977c8
Source dataset
uspto-grants-1999_07
Patent number
US05929098

Linked notes

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