1-Pentanethiol → 3-Chloropropyl pentyl sulfide

HRID 1034122Notes

Reaction equation

HRID 1034122 reaction equation
[H-].[Na+].[CH2:3]([SH:8])[CH2:4][CH2:5][CH2:6][CH3:7].[Na].[Cl:10][CH2:11][CH2:12][CH2:13]I>O1CCCC1>[CH2:3]([S:8][CH2:13][CH2:12][CH2:11][Cl:10])[CH2:4][CH2:5][CH2:6][CH3:7]

Participants

6

Reactant 4

HCID 80671-PentanethiolHCID 24758Sodium hydrideHCID 813631-Chloro-3-iodopropaneHCID 5360545Sodium

Product 1

HCID 190231263-Chloropropyl pentyl sulfideYield 59%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

A suspension of sodium hydride (4.0 g, 100 mmole) in dry tetrahydrofuran (350 mL) under a nitrogen atmosphere was cooled in an ice bath. Pentyl mercaptan (10.8 g, 100 mmole) was added dropwise over 10 minutes. The resulting suspension of sodium alkylmercaptide was added in portions over 30 minutes to a stirred solution of 1-chloro-3-iodopropane (20.44 g, 100 mmole) in tetrahydrofuran (450 mL) that had been cooled to -78° C. The mixture was allowed to warm to ambient temperature overnight, then washed with brine, dried over MgSO4, and concentrated under vacuum. The resultant oil was distilled under water aspirator pressure to yield the desired product (10.67 g, 59% yield), b.p. 113°-119° C. (20 mm Hg).

Workup

  1. temperaturewas cooled in an ice bath
  2. temperatureto warm to ambient temperature overnight
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under vacuum
  6. distillationThe resultant oil was distilled under water aspirator pressure

Sources & evidence

ORD record
ord-4a972ec696ce4b1cb105a2fbe00711b9
Source dataset
uspto-grants-1994_05
Patent number
US05314790

Reaction notes

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