Triethylamine → HCID 19849008, compound

HRID 1608267Notes

Reaction equation

HRID 1608267 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8][NH2:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].C(N(CC)CC)C.[C:19](Cl)(=[O:22])[CH:20]=[CH2:21]>ClCCl>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][NH:9][C:19](=[O:22])[CH:20]=[CH2:21])=[CH:10][CH:11]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 291474-Nitrobenzylamine

Product 1

HCID 19849008HCID 19849008, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of freshly prepared 4-nitrobenzylamine (3.8 g) in dry dichloromethane (100 ml) containing triethylamine (3.5 ml) was added dropwise to acryloyl chloride (2.2 ml) in dry dichloromethane (100 ml), over 20 min during which time the temperature was kept between -15° and -7°. The reaction mixture was stirred at this temperature for 0.5 h. and then allowed to reach room temperature over a period of 1.25 h. The resulting solution was washed with 2N hydrochloric acid (50 ml), water (50 ml), aqueous 8% sodium bicarbonate solution, and water (50 ml), dried (MgSO4) and evaporated to dryness to afford a solid (3.89 g). This which was triturated with cyclohexane (about 400 ml) to give the title compound as a powder (3.654 g) m.p. 119°-121°.

Workup

  1. customwas kept between -15° and -7°
  2. waitto reach room temperature over a period of 1.25 h
  3. washThe resulting solution was washed with 2N hydrochloric acid (50 ml), water (50 ml), aqueous 8% sodium bicarbonate solution, and water (50 ml)
  4. dry with materialdried (MgSO4)
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-aacbd2cccf8740c0a5a1ded2ce9462fd
Source dataset
uspto-grants-1989_09
Patent number
US04870096

Reaction notes

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