3-Chloro-1-propanol → HCID 12497320, compound

HRID 2375295Notes

Reaction equation

HRID 2375295 reaction equation
Cl[CH2:2][CH2:3][CH2:4][OH:5].[N+:6]([C:9]1[CH:14]=[CH:13][C:12]([SH:15])=[CH:11][CH:10]=1)([O-:8])=[O:7].[OH-].[Na+]>O>[OH:5][CH2:4][CH2:3][CH2:2][S:15][C:12]1[CH:13]=[CH:14][C:9]([N+:6]([O-:8])=[O:7])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 123133-Chloro-1-propanolHCID 14798Sodium HydroxideHCID 158094-Nitrobenzenethiol

Product 1

HCID 12497320HCID 12497320, compoundYield 98.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

3-Chloropropanol (6.0 g, 63.5 mmol) was added dropwise to a solution of 4-nitrothiophenol (8.2 g, 52.9 mmol) and sodium hydroxide (3.2 g) in water (120 ml) stirred and heated at 80° C. under nitrogen and the mixture heated at 80° C. for 205 minutes. The mixture was allowed to cool and then extracted with EtOAc (2×100 ml). The extracts were combined, washed with water (50 ml) and brine (50 ml), dried and evaporated to give the title compound (11.1 g, 98%). NMR (CDCl3) 1.99 (m, 2H), 3.18 (t, 2H), 3.81 (m, 2H), 7.35 (d, 2H), 8.13 (d, 2H).

Workup

  1. temperaturethe mixture heated at 80° C. for 205 minutes
  2. temperatureto cool
  3. extractionextracted with EtOAc (2×100 ml)
  4. washwashed with water (50 ml) and brine (50 ml)
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-9da127c41cb04ce7aba465846661e345
Source dataset
uspto-grants-2008_12
Patent number
US07465728B2

Reaction notes

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