O,O-Dipyridin-2-yl carbonothioate → 2-(4-Isothiocyanatophenoxy)-3-methylpyridine

HRID 410177Notes

Reaction equation

HRID 410177 reaction equation
[CH3:1][C:2]1[C:3]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.[C:16](=[S:31])(OC1C=CC=CN=1)OC1C=CC=CN=1>C(Cl)Cl>[N:15]([C:12]1[CH:11]=[CH:10][C:9]([O:8][C:3]2[C:2]([CH3:1])=[CH:7][CH:6]=[CH:5][N:4]=2)=[CH:14][CH:13]=1)=[C:16]=[S:31]

Participants

4

Reactant 2

HCID 719784O,O-Dipyridin-2-yl carbonothioateHCID 593268084-[(3-methyl-2-pyridinyl)oxy]Benzenamine

Product 1

HCID 593269372-(4-Isothiocyanatophenoxy)-3-methylpyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a round bottomed flask were added 4-(3-methylpyridin-2-yloxy)benzenamine (100 mg, 0.5 mmol), O,O-dipyridin-2-yl carbonothioate (122 mg, 0.52 mmol) and DCM (2 mL). The reaction mixture was stirred at RT for 16 h. The reaction was partitioned between DCM and water, brine. The aqueous layer was extracted with DCM and the combined organics was dried (Na2SO4) and concentrated to give 2-(4-isothiocyanatophenoxy)-3-methylpyridine as tan solid. MS (ESI, pos. ion) m/z: 243.1 (M+1).

Workup

  1. customThe reaction was partitioned between DCM and water, brine
  2. extractionThe aqueous layer was extracted with DCM
  3. dry with materialthe combined organics was dried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0591dbda7ee84f18b76c1b4bf1c358dc
Source dataset
uspto-grants-2014_06
Patent number
US08759532B2

Reaction notes

Loading…