2-Chloro-5-nitroanisole → 2-Methoxy-4-nitrobenzene-1-thiol

HRID 1916363Notes

Reaction equation

HRID 1916363 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[O:11][CH3:12].O.O.O.O.O.O.O.O.O.[S-2:22].[Na+].[Na+]>C(O)C.O>[CH3:12][O:11][C:3]1[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=1[SH:22]

Participants

5

Reactant 2

HCID 705192-Chloro-5-nitroanisoleHCID 73972Sodium sulfide nonahydrate

Product 1

HCID 221487412-Methoxy-4-nitrobenzene-1-thiol

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a suspension of 2-chloro-5-nitroanisole (1.00 g; 5.33 mmol) in 10 mL of ethanol at rt was added a solution of sodium sulfide nonahydrate (1.30 g; 5.41 mmol) in 1.4 mL of water and 0.8 mL of ethanol in three portions over 3 minutes. The resulting suspension was heated at 100° C. for 10 min. The suspension was cooled and concentrated under reduced pressure to a dark solid which was used immediately in the next step. HPLC 2.23 min retention time; LCMS (ES): m/z 186 [M+H]+.

Workup

  1. temperatureThe suspension was cooled
  2. concentrationconcentrated under reduced pressure to a dark solid which
  3. customHPLC 2.23 min retention time

Sources & evidence

ORD record
ord-f52fcc9dce9340b5a6400a2f4c841b42
Source dataset
uspto-grants-2013_12
Patent number
US08618115B2

Reaction notes

Loading…