4,5-Dichloro-2-nitroaniline → HCID 18421956, compound

HRID 1281702Notes

Reaction equation

HRID 1281702 reaction equation
[CH3:1][S-:2].[Na+].[Cl:4][C:5]1[C:11](Cl)=[CH:10][C:8]([NH2:9])=[C:7]([N+:13]([O-:15])=[O:14])[CH:6]=1>CN(C)C=O>[Cl:4][C:5]1[C:11]([S:2][CH3:1])=[CH:10][C:8]([NH2:9])=[C:7]([N+:13]([O-:15])=[O:14])[CH:6]=1

Participants

4

Reactant 2

HCID 811494,5-Dichloro-2-nitroanilineHCID 4378561Sodium methanethiolate2×

Product 1

HCID 18421956HCID 18421956, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium methanethiolate (4.06 g, 58.0 mmol, Aldrich) was suspended in 80 ml dimethylformamide. 4,5-Dichloro-2-nitroaniline (10.0 g, 48.3 mmol, Aldrich) was added portionwise. Additional sodium methanethiolate (4.38 g, 62.5 mmol) was added over several h until starting material was consumed. The reaction mixture was poured into water (400 ml) and the resulting precipitate was collected by filtration and dried to give 9.05 g (41.4 mmol, 86% yield) of the title compound. 1H NMR (CDCl3) δ8.15 (s, 1H), 6.44 (s, 1H), 2.52 (s, 3H).

Workup

  1. customwas consumed
  2. additionThe reaction mixture was poured into water (400 ml)
  3. filtrationthe resulting precipitate was collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-36b61ef741314f94ab16d0be4b3baed5
Source dataset
uspto-grants-2002_09
Patent number
US06455507B1

Reaction notes

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