Triethylamine → 3-(4-Chlorophenyl)-2-methyl-acryloyl azide

HRID 1432850Notes

Reaction equation

HRID 1432850 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[C:9]([CH3:13])[C:10](O)=[O:11])=[CH:4][CH:3]=1.C(N(CC)CC)C.ClC(OCC)=O.[N-:27]=[N+:28]=[N-:29].[Na+]>CC(C)=O.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[C:9]([CH3:13])[C:10]([N:27]=[N+:28]=[N-:29])=[O:11])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 33557Sodium AzideHCID 2351143-(4-Chlorophenyl)-2-methylprop-2-enoic acid

Product 1

HCID 542762533-(4-Chlorophenyl)-2-methyl-acryloyl azideYield 87.7%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

To a solution of 3-(4-chlorophenyl)-2-methyl-acrylic acid (11.2 g, 57 mmol) in 500 mL of acetone at 0° C. is added triethyl amine (9.6 mL, 68 mmol) followed by ethyl chloroformate (6.2 mL, 63 mmol). The solution is allowed to warm to ambient temperatures. After 2 h, sodium azide (5.6 g, 86 mmol) in 35 mL of H2O is added. After addition, the solution is stirred for 2 hours. The solution is diluted with H2O (100 mL). The resulting solid is collected by filtration giving the title compound as a white solid (11.1 g, 50 mmol). 1H NMR (CDCl3, 300 MHz) δ7.67 (s, 1H), 3.38 (m, 4H), 2.10 9s, 3H).

Workup

  1. temperatureto warm to ambient temperatures
  2. additionAfter addition
  3. filtrationThe resulting solid is collected by filtration

Sources & evidence

ORD record
ord-6bcd48efa069475598b0c78c49ceb48f
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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