Acetic Acid → HCID 57054047, compound

HRID 1508784Notes

Reaction equation

HRID 1508784 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][CH:4]=1.C(O)(=O)C.[O-:16][C:17]#[N:18].[Na+]>O1CCCC1>[CH3:1][N:2]([C:3]1[CH:4]=[CH:5][C:6]([N+:9]([O-:11])=[O:10])=[CH:7][CH:8]=1)[C:17]([NH2:18])=[O:16]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 7483N-Methyl-4-nitroanilineHCID 517096Sodium Cyanate

Product 1

HCID 57054047HCID 57054047, compoundYield 25.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 250-mL round bottom flask was charged with N-methyl-4-nitroaniline (1.94 g, 12.7 mmol) in tetrahydrofuran (50 mL). To this stirred solution at rt was added acetic acid (14.6 mL, 255 mmol) and sodium cyanate (8.29 g, 127.5 mmol). After 24 h, the reaction mixture was concentrated under reduced pressure. The residue was suspended in water (100 mL) and the resultant solid was isolated by filtration, washing sequentially with dichloromethane and ethyl acetate to afford the title compound (0.63 g, 25%) as a yellow solid. MW=195.18. 1H NMR (DMSO-d6, 500 MHz) δ 8.19-8.14 (m, 2H), 7.58-7.54 (m, 2H), 6.54 (br s, 2H), 3.27 (s, 3H).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customthe resultant solid was isolated by filtration
  3. washwashing sequentially with dichloromethane and ethyl acetate

Sources & evidence

ORD record
ord-741903b9c72e4b7fa5f7bdb0beef1462
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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