Triethylamine → Methyl 4-[(2-chloroethyl)amino]-3,5-dinitrobenzoate

HRID 852604Notes

Reaction equation

HRID 852604 reaction equation
Cl[C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N+:15]([O-:17])=[O:16].Cl.[Cl:19][CH2:20][CH2:21][NH2:22].CCN(CC)CC>CO>[Cl:19][CH2:20][CH2:21][NH:22][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N+:15]([O-:17])=[O:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 96161Methyl 4-chloro-3,5-dinitrobenzoateHCID 97937372-Chloroethylamine hydrochloride

Product 1

HCID 86161362Methyl 4-[(2-chloroethyl)amino]-3,5-dinitrobenzoateYield 156%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 4-chloro-3,5-dinitrobenzoate (D25a) (5.0 g, 19.2 mmol, 1 equiv) in MeOH (300 ml) was added 2-chloroethylamine hydrochloride (4.64 mg, 40 mmol, 2.1 equiv) and NEt3 (5.5 ml, 40 mmol, 2.1 equiv) and the resulting mixture was refluxed for 5 min then cooled to room temperature. Most of the solvent was evaporated in vacuo and the residue filtered off to give methyl 4-[(2-chloroethyl)amino]-3,5-dinitrobenzoate (D208) (9 g, 156%) as a yellow solid which was used in the next step without further purification. [M+H]+=304.1, RT=3.06 min.

Workup

  1. temperaturethe resulting mixture was refluxed for 5 min
  2. customMost of the solvent was evaporated in vacuo
  3. filtrationthe residue filtered off

Sources & evidence

ORD record
ord-07d3f01a5617480e8a823d4829f2536e
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

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