Butanethiol → HCID 13726875, compound

HRID 1583885Notes

Reaction equation

HRID 1583885 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[CH3:13][CH2:14][CH2:15][CH2:16][SH:17].[Na]>>[N+:10]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:2]=1[S:17][CH2:16][CH2:15][CH2:14][CH3:13])[CH:6]=[O:7])([O-:12])=[O:11]

Participants

4

Reactant 3

HCID 8012ButanethiolHCID 855054-Chloro-3-nitrobenzaldehydeHCID 5360545Sodium

Product 1

HCID 13726875HCID 13726875, compound

Procedure

4-Chloro-3-nitrobenzaldehyde (25.0 g) was added to a solution of sodium n-butylthiolate (1 equiv; prepared by addition of n-butylthiol to an equimolar amount of sodium dissolved in absolute alcohol) in absolute alcohol (300 ml) and the mixture was heated under reflux for 4 hr. On cooling, the mixture was filtered and the filtrate was evaporated under reduced pressure. The residue was purified by column chromatography over silica gel with dichloromethane elution to give 3-nitro-4-(n-butylthio)benzaldehyde as yellow crystals, mp 93° C. Pmr spectrum (CDCl3 ; δ in ppm): 0.99 (3H, t); 1.66 (4H, m); 3.04 (2H, t); 7.56 (1H, d); 8.05 (1H, dofd); 8.69 (1H, d); 10.00 (1H, s).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 hr
  3. temperatureOn cooling
  4. filtrationthe mixture was filtered
  5. customthe filtrate was evaporated under reduced pressure
  6. customThe residue was purified by column chromatography over silica gel with dichloromethane elution

Sources & evidence

ORD record
ord-3c20bc7cee9f4cb696868d9f99bf0501
Source dataset
uspto-grants-1985_11
Patent number
US04555263

Reaction notes

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