Triethylamine → HCID 11264879, compound

HRID 1447454Notes

Reaction equation

HRID 1447454 reaction equation
Cl[N:2]1[C:6](=[O:7])[CH2:5][CH2:4][C:3]1=[O:8].[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([SH:17])=[CH:13][CH:12]=1.C(N(CC)CC)C>C1C=CC=CC=1>[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([S:17][N:2]2[C:6](=[O:7])[CH2:5][CH2:4][C:3]2=[O:8])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 127654-MethoxybenzenethiolHCID 31398Chlorosuccinimide

Product 1

HCID 11264879HCID 11264879, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent3×

Procedure

A mixture of 17.1 g. (128 mmole) of N-chlorosuccinimide and 700 ml. of benzene is treated with 15 g. (107 mmole) of p-methoxythiophenol dissolved in 125 ml. of benzene. After 75 minutes, the resulting orange solution is cooled to 15° and 13.0 g. (128 mmole) of triethylamine in 125 ml. of benzene is added over a period of 25 minutes. The cooling bath is removed and the reaction is stirred at room temperature for an additional 45 minutes. The reaction mixture is then filtered and the organic solution is rinsed with three 200 ml. portions of water, 200 ml. of brine and dried (MgSO4). Removal of the solvents in vacuo gives 27.0 g. of crude product. Recrystallization from chloroform-hexane gives 21.2 g. of

Workup

  1. additionA mixture of 17.1 g
  2. temperaturethe resulting orange solution is cooled to 15°
  3. customThe cooling bath is removed
  4. filtrationThe reaction mixture is then filtered
  5. washthe organic solution is rinsed with three 200 ml
  6. dry with materialof brine and dried (MgSO4)
  7. customRemoval of the solvents in vacuo
  8. customgives 27.0 g
  9. customRecrystallization from chloroform-hexane
  10. customgives 21.2 g

Sources & evidence

ORD record
ord-292e697cdb564934934816e8145f1539
Source dataset
uspto-grants-1982_02
Patent number
US04316906

Reaction notes

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