Ammonia → 2-methoxy-N-[3-(methylthio)-2-nitrophenyl]acetamide

HRID 869535

Reaction equation

HRID 869535 reaction equation
[CH3:1][S:2][C:3]1[C:4]([N+:10]([O-:12])=[O:11])=[C:5]([CH:7]=[CH:8][CH:9]=1)[NH2:6].N1C=CC=CC=1.[CH3:19][O:20][CH2:21][C:22](Cl)=[O:23].N>CC(N(C)C)=O.O.CO>[CH3:19][O:20][CH2:21][C:22]([NH:6][C:5]1[CH:7]=[CH:8][CH:9]=[C:3]([S:2][CH3:1])[C:4]=1[N+:10]([O-:12])=[O:11])=[O:23]

Participants

8

Reactant 4

HCID 222AmmoniaHCID 1049PyridineHCID 96623Methoxyacetyl chlorideHCID 109761553-(Methylthio)-2-nitroaniline

Product 1

HCID 867213652-methoxy-N-[3-(methylthio)-2-nitrophenyl]acetamideYield 91%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Procedure

[step 2] 3-(Methylthio)-2-nitroaniline (1.0 g, 5.4 mmol) obtained in step 1 was dissolved in DMA (5.4 mL), pyridine (0.44 mL, 5.4 mmol) and 2-methoxyacetyl chloride (1.49 mL, 16 mmol) were added, and the mixture was stirred at room temperature for 2 hr. To the reaction solution were added methanol and aqueous ammonia, and the mixture was stirred at room temperature for 30 min. Water was added, and the crystals were collected by filtration, and dried to give 2-methoxy-N-[3-(methylthio)-2-nitrophenyl]acetamide (1.26 g, 91%).

Workup

  1. stirringthe mixture was stirred at room temperature for 30 min
  2. filtrationthe crystals were collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-2cc65d3a3b3a4620afaf63eea3ce3d7a
Source dataset
uspto-grants-2015_03
Patent number
US08969345B2

Linked notes

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