Methanethiol → 1-[(Methylsulfanyl)methyl]-2-nitrobenzene

HRID 1702522Notes

Reaction equation

HRID 1702522 reaction equation
C[O-].[Na+].[CH3:4][SH:5].[N+:6]([C:9]1[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=1[CH2:11]Cl)([O-:8])=[O:7]>CO.O>[CH3:4][S:5][CH2:11][C:10]1[CH:13]=[CH:14][CH:15]=[CH:16][C:9]=1[N+:6]([O-:8])=[O:7]

Participants

6

Reactant 3

HCID 878MethanethiolHCID 119212-Nitrobenzyl chlorideHCID 10942334Sodium Methoxide

Product 1

HCID 130574171-[(Methylsulfanyl)methyl]-2-nitrobenzeneYield 120.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

To a stirred solution of 10.8 g (0.2 mol) of sodium methoxide in 70 ml of methanol at room temperature was added dropwise 12 ml (10.8 g, 0.22 mol) of methyl mercaptan through a gas addition funnel connected to a dry-ice condenser. The resulting mixture was stirred at room temperature for 1 hour and then added dropwise to a stirred solution of 30.0 g (0.175 mole) of o-nitrobenzyl chloride in 120 ml of methanol over 1 hour, while the temperature rose to 40° C. The reaction mixture was then diluted with 300 ml of water, and extracted 3 times with methylene chloride. The methylene chloride extracts were washed with dilute hydrochloric acid, dried, and concentrated to afford 38.6 g (96%) of yellow oil.

Workup

  1. additionthrough a gas addition funnel
  2. customconnected to a dry-ice condenser
  3. customrose to 40° C
  4. extractionextracted 3 times with methylene chloride
  5. washThe methylene chloride extracts were washed with dilute hydrochloric acid
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c2ee2b2f1fea4b81a2a48b519ddbddc5
Source dataset
uspto-grants-1982_09
Patent number
US04348220

Reaction notes

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