HCID 13422541, compound → HCID 53720893, compound

HRID 224802Notes

Reaction equation

HRID 224802 reaction equation
[O:1]1[C:7]2[CH:8]=[CH:9][CH:10]=[C:11]([OH:12])[C:6]=2[O:5][CH:4]=[CH:3][CH2:2]1.[Cl:13][C:14]([Cl:22])([Cl:21])[S:15][N:16]([CH3:20])[C:17](Cl)=[O:18]>C1C=CC=CC=1>[O:1]1[C:7]2[CH:8]=[CH:9][CH:10]=[C:11]([O:12][C:17](=[O:18])[N:16]([S:15][C:14]([Cl:22])([Cl:21])[Cl:13])[CH3:20])[C:6]=2[O:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 13422541HCID 13422541, compoundHCID 23330630HCID 23330630, compound

Product 1

HCID 53720893HCID 53720893, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

1.3 G. of sodium hydride (50% dispersion in oil) are washed twice with petroleum ether (40°-45° C.) and then suspended in 30 ml. of absolute benzene in a flask. 4.15 G. 1,5-benzodioxepin-6-ol (0.025 mol) are added stepwise with stirring and under a nitrogen atmosphere. This mixture is stirred for 30 minutes at room temperature and then a solution of 6.7 g. of N-trichloromethylthio-N-methyl carbamyl chloride (freshly prepared) in 30 ml. of absolute benzene is added over a 30 minute period. The resulting mixture is stirred at room temperature for four hours, then poured into 50 ml. of ice water and extracted three times with 30 ml. of benzene. The benzene extracts are washed with water, dried over sodium sulfate and evaporated. The crude product is chromatographed on silica gel and eluted with dichloromethylene. On evaporation, 3,4-dihydro-2H-1,5-benzodioxepin-6-yl-[(trichloromethyl)thio]-methylcarbamate is obtained as a yellow oil; MD24 :1.5658.

Workup

  1. washof sodium hydride (50% dispersion in oil) are washed twice with petroleum ether (40°-45° C.)
  2. stirringThis mixture is stirred for 30 minutes at room temperature
  3. stirringThe resulting mixture is stirred at room temperature for four hours
  4. additionpoured into 50 ml
  5. extractionof ice water and extracted three times with 30 ml
  6. washThe benzene extracts are washed with water
  7. dry with materialdried over sodium sulfate
  8. customevaporated
  9. customThe crude product is chromatographed on silica gel
  10. washeluted with dichloromethylene
  11. customOn evaporation

Sources & evidence

ORD record
ord-b3f69f360b9a4fbf853a25786a72ae95
Source dataset
uspto-grants-1980_11
Patent number
US04234598

Reaction notes

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