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

HRID 1880044Notes

Reaction equation

HRID 1880044 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-7b96d52b347a4b4dbe518346b9cca9f2
Source dataset
uspto-grants-2012_11
Patent number
US08318718B2

Reaction notes

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