Water → 2-amino-3-nitro-5-methyl-N-(beta-hydroxyethyl)-N-tosylaniline

HRID 2081894Notes

Reaction equation

HRID 2081894 reaction equation
[NH2:1][C:2]1[C:18]([N+:19]([O-:21])=[O:20])=[CH:17][C:16]([CH3:22])=[CH:15][C:3]=1[NH:4][S:5]([C:8]1[CH:14]=[CH:13][C:11]([CH3:12])=[CH:10][CH:9]=1)(=[O:7])=[O:6].[O-2].[Ca+2].[CH2:25]([OH:28])[CH2:26]Br.O>CN(C=O)C>[NH2:1][C:2]1[C:18]([N+:19]([O-:21])=[O:20])=[CH:17][C:16]([CH3:22])=[CH:15][C:3]=1[N:4]([CH2:26][CH2:25][OH:28])[S:5]([C:8]1[CH:9]=[CH:10][C:11]([CH3:12])=[CH:13][CH:14]=1)(=[O:7])=[O:6]

Participants

6

Reactant 4

HCID 962WaterHCID 108982-BromoethanolHCID 6850728CalciumoxideHCID 19778832HCID 19778832, compound

Product 1

HCID 197788282-amino-3-nitro-5-methyl-N-(beta-hydroxyethyl)-N-tosylaniline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.087 mol (28 g) of 2-amino-3-nitro-5-methyl-N-tosylaniline is dissolved in 85 ml of DMF heated beforehand on a boiling water-bath. 9.7 g of quicklime are then added and 0.174 mol (21.75 g) of glycol bromohydrin is then introduced gradually, in the course of 30 minutes and whilst stirring, the heating on the boiling water-bath being maintained. After 11/2 hours, the reaction medium is filtered hot and the filtrate is then poured into 250 ml of iced water. The expected product precipitates. It is filtered off, washed with water and dried in vacuo. After recrystallisation from acetic acid and drying in vacuo, it melts at 201° C.

Workup

  1. filtrationAfter 11/2 hours, the reaction medium is filtered hot
  2. additionthe filtrate is then poured into 250 ml of iced water
  3. customThe expected product precipitates
  4. filtrationIt is filtered off
  5. washwashed with water
  6. customdried in vacuo
  7. customAfter recrystallisation from acetic acid
  8. customdrying in vacuo, it melts at 201° C.

Sources & evidence

ORD record
ord-dc111678df72447d8cc19e3b82725a92
Source dataset
uspto-grants-1993_02
Patent number
US05186717

Reaction notes

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