2-Methoxyethylamine → HCID 21506036, compound

HRID 918628Notes

Reaction equation

HRID 918628 reaction equation
Cl[C:2]1[C:10]([S:11](=[O:14])(=[O:13])[NH2:12])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:15]([O-:17])=[O:16].[CH3:18][O:19][CH2:20][CH2:21][NH2:22]>C(O)C>[CH3:18][O:19][CH2:20][CH2:21][NH:22][C:2]1[C:10]([S:11](=[O:14])(=[O:13])[NH2:12])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:15]([O-:17])=[O:16]

Participants

4

Reactant 2

HCID 80182-MethoxyethylamineHCID 898934-Chloro-3-nitro-5-sulphamoylbenzoic acid

Product 1

HCID 21506036HCID 21506036, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 4-chloro-3-nitro-5-sulphamyl-benzoic acid (4.2 g), 2-methoxyethylamine (5.6 g), and 50% ethanol (10 ml) was heated to 60°C for 1 hour. The ethanol was distilled off under reduced pressure, and the resulting 4-(2-methoxyethylamino)-3-nitro-5-sulphamyl-benzoic acid was precipitated by addition of 4N hydrochloric acid until pH 2. After recrystallization from water, the melting point was 192°-194°C. The compound crystallized with 1 molecule of water of crystallization.

Workup

  1. distillationThe ethanol was distilled off under reduced pressure
  2. customthe resulting 4-(2-methoxyethylamino)-3-nitro-5-sulphamyl-benzoic acid was precipitated by addition of 4N hydrochloric acid until pH 2
  3. customAfter recrystallization from water
  4. customThe compound crystallized with 1 molecule of water of crystallization

Sources & evidence

ORD record
ord-9325a41350b948f5ab22b2f386f865d8
Source dataset
uspto-grants-1976_07
Patent number
US03971819

Reaction notes

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