Methyl sulfate(1-) → 2-amino-3-nitro-5-methyl-N-methyl-N-tosylaniline

HRID 2081897Notes

Reaction equation

HRID 2081897 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].S([O-])(O[CH3:27])(=O)=O>[OH-].[Na+]>[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]([CH3:27])[S:5]([C:8]1[CH:9]=[CH:10][C:11]([CH3:12])=[CH:13][CH:14]=1)(=[O:7])=[O:6]

Participants

4

Reactant 2

HCID 4694097Methyl sulfate(1-)2×HCID 19778832HCID 19778832, compound

Product 1

HCID 197788512-amino-3-nitro-5-methyl-N-methyl-N-tosylaniline

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent2×

Conditions

Temperature
10 °C

Procedure

0.246 mol (79 g) of 2-amino-3-nitro-5-methyl-N-tosylaniline is dissolved in 260 ml of normal sodium hydroxide solution at 40° C. 0.286 mol (30 ml) of methyl sulphate is added gradually in the course of 3 hours, the temperature being kept at about 40° C. Towards the end of the addition of the methyl sulphate, the pH of the reaction medium is kept alkaline by simultaneously adding 20 ml of normal sodium hydroxide solution. After cooling to about 10° C., the expected product which has precipitated is filtered off. It is washed with a normal sodium hydroxide solution and then with water and recrystallised from acetic acid. After drying in vacuo, it melts at 208° C.

Workup

  1. custombeing kept at about 40° C
  2. customthe expected product which has precipitated
  3. filtrationis filtered off
  4. washIt is washed with a normal sodium hydroxide solution
  5. customwith water and recrystallised from acetic acid
  6. customAfter drying in vacuo, it melts at 208° C.

Sources & evidence

ORD record
ord-55583f1fe381426d900637c4d2f0d19c
Source dataset
uspto-grants-1993_02
Patent number
US05186717

Reaction notes

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