Hydrochloric Acid → HCID 59325909, compound

HRID 503676Notes

Reaction equation

HRID 503676 reaction equation
[NH2:1][CH2:2][CH2:3][OH:4].[Cl:5][C:6]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][C:12]([N+:18]([O-:20])=[O:19])=[CH:11][C:7]=1[C:8](Cl)=[O:9].Cl>O>[Cl:5][C:6]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][C:12]([N+:18]([O-:20])=[O:19])=[CH:11][C:7]=1[C:8]([NH:1][CH2:2][CH2:3][OH:4])=[O:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 700EthanolamineHCID 12897330HCID 12897330, compound

Product 1

HCID 59325909HCID 59325909, compoundYield 56.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Aminoethanol (2.9 g, 47 mmol) in 5 mL of water was added in one portion to a solution of crude 2-chloro-3,5-dinitrobenzoic acid chloride [prepared from 2-chloro-3,5-dinitrobenzoic acid 11 (5.0 g, 18.3 mmol) with SOCl2] in Me2CO (50 mL) while cooling in an ice-bath. The mixture was stirred for 30 min, then acidified with 1N HCl to pH4-5 and concentrated under reduced pressure to remove the Me2CO. EtOAc (100 mL) was added, and after 2 h a white solid was collected, washed with EtOAc and air-dried to give 2-chloro-3,5-dinitro-N-(2-hydroxyethyl)benzamide (12b) (3.0 g, 36%):

Workup

  1. temperaturewhile cooling in an ice-bath
  2. concentrationconcentrated under reduced pressure
  3. customto remove the Me2CO
  4. additionEtOAc (100 mL) was added
  5. customafter 2 h a white solid was collected
  6. washwashed with EtOAc
  7. customair-dried

Sources & evidence

ORD record
ord-9a272df3d3924ef0a9c3705b887d375e
Source dataset
uspto-grants-2010_08
Patent number
US07776924B2

Reaction notes

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