4-Methyl-3-nitroaniline → HCID 50998334, compound

HRID 2235510Notes

Reaction equation

HRID 2235510 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].C(N(CC)CC)C.[C:19](Cl)(Cl)=[S:20]>C1COCC1.O>[N:6]([C:5]1[CH:7]=[CH:8][C:2]([CH3:1])=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1)=[C:19]=[S:20]

Participants

6

Reactant 3

HCID 83904-Methyl-3-nitroanilineHCID 8471TriethylamineHCID 10040Thiophosgene

Product 1

HCID 50998334HCID 50998334, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 4-methyl-3-nitroaniline (1.00 g, 6.57 mmol) and triethylamine (2.75 ml, 19.7 mmol) in THF (150 ml) was added dropwise thiophosgene (0.55 ml) at 0° C. After addition, the reaction mixture was allowed to stir at room temperature for 15 h. The mixture was diluted with water and extracted with ether. The extract was washed with water and brine, dried over magnesium sulfate, and concentrated under vacuum to afford 1.04 g of the title compound.

Workup

  1. additionAfter addition
  2. extractionextracted with ether
  3. washThe extract was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-a33dc381f74f491bb5d027691aa3a809
Source dataset
uspto-grants-2010_05
Patent number
US07714009B2

Reaction notes

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