Sulfamide → N-(2-cyano-3-methylphenyl)sulfamide

HRID 711631

Reaction equation

HRID 711631 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:3]=1[C:4]#[N:5].[S:11](N)([NH2:14])(=[O:13])=[O:12]>O1CCOCC1>[C:4]([C:3]1[C:6]([CH3:10])=[CH:7][CH:8]=[CH:9][C:2]=1[NH:1][S:11]([NH2:14])(=[O:13])=[O:12])#[N:5]

Participants

4

Reactant 2

HCID 82267SulfamideHCID 2799732-Amino-6-methylbenzonitrile

Product 1

HCID 67097231N-(2-cyano-3-methylphenyl)sulfamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 2-amino-6-methylbenzonitrile (1.32 g, 10 mmol) and sulfamide (4.81 g, 50 mmol) in dry 1,4-dioxane (50 mL) was refluxed under nitrogen for 3 days. After the reaction mixture was cooled down to room temperature, the precipitate was filtered and washed with dioxane. The filtrate was concentrated under reduced pressure, and the residue was purified by chromatography on silica gel eluting with EtOAc/hexanes (3:7) to give the title compound as a pale-white solid. 1H NMR (400 MHz, DMSO-d6) δ 2.44 (s, 3H), 7.19-7.21 (m, 3H), 7.39-7.41 (d, J=8.4 Hz, 1H), 7.53 (t, J=8.0 Hz, 1H), 9.41 (s, 1H).

Workup

  1. filtrationthe precipitate was filtered
  2. washwashed with dioxane
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe residue was purified by chromatography on silica gel eluting with EtOAc/hexanes (3:7)

Sources & evidence

ORD record
ord-347f0b4d6d274ab5a4efd9b6d82d3170
Source dataset
uspto-grants-2015_11
Patent number
US09181276B2

Linked notes

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