HCID 9839432, compound → HCID 9817460, compound

HRID 369489Notes

Reaction equation

HRID 369489 reaction equation
[Cl:1][CH2:2][CH2:3][N:4]([CH2:17][CH2:18][Cl:19])[C:5]1[C:14]([CH3:15])=[CH:13][C:12]([CH3:16])=[CH:11][C:6]=1[C:7]([O:9]C)=[O:8]>Cl>[Cl:1][CH2:2][CH2:3][N:4]([CH2:17][CH2:18][Cl:19])[C:5]1[C:14]([CH3:15])=[CH:13][C:12]([CH3:16])=[CH:11][C:6]=1[C:7]([OH:9])=[O:8]

Participants

3

Reactant 1

HCID 9839432HCID 9839432, compound

Product 1

HCID 9817460HCID 9817460, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A suspension of methyl 2-bis(2'-chloroethyl)amino-3,5-dimethylbenzoate (5.6 g, 0.018 mol) in concentrated HCl (37% w/w in H2O, 150 mL) was heated to refluxing under N2 for 8 hours. The reaction mixture was treated with ice/H2O (200 mL), extracted wit chloroform (3×150 mL). The organic solution was concentrated to given the product 2-bis(2'-chloroethyl)amino-3,5-dimethylbenzoic acid as a white solid (5.1 g, 96%). 1H NMR (300 MHz, CDCl3): 8.01 (d, J=1.5 Hz, 1H), 7.23 (dd, J=1.5, 0.6 Hz, 1H), 3.6 (m, 8H), 2.43 (s, 3H), 2.35 (s, 3H). ESMS calcd (C13H17Cl2NO2): 289.1; found: 290.1 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureto refluxing under N2 for 8 hours
  3. extractionextracted wit chloroform (3×150 mL)
  4. concentrationThe organic solution was concentrated

Sources & evidence

ORD record
ord-3434d590aab24c83928dca235c9e0a5c
Source dataset
uspto-grants-2000_10
Patent number
US06137003

Reaction notes

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