Pyridine → Isopropyl (chlorosulfinyl)(phenyl)carbamate

HRID 443746Notes

Reaction equation

HRID 443746 reaction equation
[C:1]1([NH:7][C:8](=[O:13])[O:9][CH:10]([CH3:12])[CH3:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[S:14](Cl)([Cl:16])=[O:15].N1C=CC=CC=1>O1CCCC1>[Cl:16][S:14]([N:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:8](=[O:13])[O:9][CH:10]([CH3:11])[CH3:12])=[O:15]

Participants

5

Reactant 3

HCID 1049Pyridine2×HCID 24386Thionyl ChlorideHCID 24685Propham

Product 1

HCID 12728807Isopropyl (chlorosulfinyl)(phenyl)carbamateYield 61.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Eighteen grams isopropyl phenylcarbamate (~0.1 mol) and 14.0 g thionyl chloride (0.12 mol) were dissolved in 50 ml dry tetrahydrofuran and protected from moisture by a calcium chloride tube. Eight grams pyridine (0.1 mol) were added dropwise while the mixture was stirring at a water bath temperature (15°-20° C.). After the addition of pyridine was completed, the mixture was stirred for 12 hours at room temperature. Pyridine hydrochloride was filtered and the solvent was removed under vacuum. The concentrated residue was diluted with hexane and filtered. The hexane was removed under vacuum and the residue was distilled, giving 16.0 g of product distilling at 113-115/0.08 mm. NMR spectrum of the product in chloroform-d-TMS gave the following absorptions: δ7.6-7.2 (m, 5H, phenyl protons), δ5.5-4.9 (m, 1H, CH) and δ1.4-1.3 (d, 6H, C(CH3)2).

Workup

  1. customprotected from moisture by a calcium chloride tube
  2. stirringthe mixture was stirred for 12 hours at room temperature
  3. filtrationPyridine hydrochloride was filtered
  4. customthe solvent was removed under vacuum
  5. additionThe concentrated residue was diluted with hexane
  6. filtrationfiltered
  7. customThe hexane was removed under vacuum
  8. distillationthe residue was distilled

Sources & evidence

ORD record
ord-bf312fb42f2541cb8fb0654ff628516a
Source dataset
uspto-grants-1981_04
Patent number
US04261897

Reaction notes

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