Tetrahydrofuran → HCID 12526269, compound

HRID 329200Notes

Reaction equation

HRID 329200 reaction equation
[CH2:1]([O:3][C:4]([N:6]=[C:7]=[S:8])=[O:5])[CH3:2].[Cl:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14][OH:15])=[CH:12][CH:11]=1.O1CCCC1>C(N(CC)CC)C>[C:4]([NH:6][C:7](=[S:8])[O:15][CH2:14][C:13]1[CH:16]=[CH:17][C:10]([Cl:9])=[CH:11][CH:12]=1)([O:3][CH2:1][CH3:2])=[O:5]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 133974-Chlorobenzyl alcoholHCID 85320Ethyl isothiocyanatoformate

Product 1

HCID 12526269HCID 12526269, compoundYield 58.2%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

90 g of ethoxycarbonyl isothiocyanate were added dropwise to a mixture of 85 g of p-chlorobenzyl alcohol, 600 ml of tetrahydrofuran and 4 ml of triethylamine and the mixture was refluxed for 24 hours and was then evaporated to dryness under reduced pressure. The residue was added to isopropyl alcohol and the precipitate formed was recovered by vacuum filtration to obtain 95 g of p-chlorobenzyl N-carbethoxy-thiocarbamate melting at 95° C.

Workup

  1. temperaturethe mixture was refluxed for 24 hours
  2. customwas then evaporated to dryness under reduced pressure
  3. additionThe residue was added to isopropyl alcohol
  4. customthe precipitate formed
  5. filtrationwas recovered by vacuum filtration

Sources & evidence

ORD record
ord-1690adbd05b541768632e944041e2278
Source dataset
uspto-grants-1977_04
Patent number
US04020076

Reaction notes

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