Hydrochloric Acid → HCID 19778832, compound

HRID 2081896Notes

Reaction equation

HRID 2081896 reaction equation
[NH2:1][C:2]1[C:8]([N+:9]([O-:11])=[O:10])=[CH:7][C:6]([CH3:12])=[CH:5][C:3]=1[NH2:4].[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1.O.Cl>N1C=CC=CC=1>[NH2:1][C:2]1[C:8]([N+:9]([O-:11])=[O:10])=[CH:7][C:6]([CH3:12])=[CH:5][C:3]=1[NH:4][S:19]([C:16]1[CH:17]=[CH:18][C:13]([CH3:23])=[CH:14][CH:15]=1)(=[O:21])=[O:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 10487280HCID 10487280, compound

Product 1

HCID 19778832HCID 19778832, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Conditions

Temperature
45 °C

Procedure

0.15 mol (25.05 g) of 2-amino-3-nitro-5-methylaniline is dissolved in 75 ml of pyridine, and 0.165 mol (31.4 g) of para-toluenesulphonyl chloride is then added gradually, whilst stirring, at between 40° and 45° C. When the addition has ended, the stirring is maintained for 1 hour at 45° C., the reaction medium is then poured into 450 ml of iced water and ther pyridine is neutralised with the aid of hydrochloric acid. The expected product which has precipitated is filtered off, washed with water and then recrystallised from acetic acid. After drying in vacuo, it melts at 184° C.

Workup

  1. additionWhen the addition
  2. customThe expected product which has precipitated
  3. filtrationis filtered off
  4. washwashed with water
  5. customrecrystallised from acetic acid
  6. customAfter drying in vacuo, it melts at 184° C.

Sources & evidence

ORD record
ord-07c24e3e047a4708822aee0ee976860a
Source dataset
uspto-grants-1993_02
Patent number
US05186717

Reaction notes

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