Methanethiol → HCID 178426720, compound

HRID 1702610Notes

Reaction equation

HRID 1702610 reaction equation
[CH3:1][SH:2].CN(C)C=[O:6].[H-].[Na+].ClC1[CH:12]=[CH:13][C:14]([N+:20]([O-:22])=[O:21])=[C:15](C=1)[C:16](O)=O.C(O[CH2:27][CH3:28])(=O)C>>[N+:20]([C:14]1[CH:15]=[CH:16][C:27]([CH3:28])=[CH:12][C:13]=1[C:1]([OH:6])=[S:2])([O-:22])=[O:21]

Participants

6

Reactant 5

HCID 878MethanethiolHCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 172865-Chloro-2-nitrobenzoic acidHCID 24758Sodium hydride

Product 1

HCID 178426720HCID 178426720, compound

Procedure

To a solution of 50 ml. of methyl mercaptan in 200 ml. of dimethylformamide was added 48 g. of sodium hydride portionwise at -40°. On completion of the ensuing reaction, 100.0 g. of 5-chloro-2-nitrobenzoic acid was added. The reaction temperature was allowed to come up to -10°, was lowered back to -40°, and the excess reagent was quenched with 1 N hydrochloric acid. After 2 hours stirring at room temperature, the product was collected, 102.3 g. (97%), mp 165°-169°. Recrystallization from methanolethyl acetate gave 52.14 g., mp. 173°-174°. The analytical sample was obtained from ethyl acetate, mp 174°-175°.

Workup

  1. customportionwise at -40°
  2. customOn completion of the ensuing reaction, 100.0 g
  3. customto come up to -10°
  4. customwas lowered back to -40°
  5. customthe excess reagent was quenched with 1 N hydrochloric acid
  6. customthe product was collected
  7. customRecrystallization from methanolethyl acetate
  8. customgave 52.14 g

Sources & evidence

ORD record
ord-391d148766e04588a90da902a3c0fa07
Source dataset
uspto-grants-1982_09
Patent number
US04348396

Reaction notes

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