Triethylamine → HCID 13044812, compound

HRID 1156386Notes

Reaction equation

HRID 1156386 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH:9]([S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-:23])=[O:22])[CH:16]=2)(=[O:14])=[O:13])[CH2:10]Cl)=[CH:4][CH:3]=1.C(N(CC)CC)C>O1CCCC1.C(OCC)C>[N+:21]([C:17]1[CH:16]=[C:15]([S:12]([C:9]([S:8][C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=2)=[CH2:10])(=[O:14])=[O:13])[CH:20]=[CH:19][CH:18]=1)([O-:23])=[O:22]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 13044801HCID 13044801, compound

Product 1

HCID 13044812HCID 13044812, compoundYield 48.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-Chloro-1-(m-nitrophenylsulfonyl)ethyl p-bromophenyl sulfide (27.1 g, 62.1 mmoles) was dissolved in 125 ml of tetrahydrofuran. The solution was diluted with 125 ml of diethyl ether and treated with 8.65 ml (6.3 g, 62.3 mmoles) of triethylamine. After one hour the mixture was filtered to remove 7.52 g (88%) of triethylamine hydrochloride, m.p. 255°-258°. Removal of solvent from the filtrate gave a yellow oil which crystallized upon scraping. Recrystallization from 25 ml of ethyl acetate and 10 ml of pentane gave 12 g (48%) of product m.p. 109°-111°.

Workup

  1. filtrationAfter one hour the mixture was filtered
  2. customto remove 7.52 g (88%) of triethylamine hydrochloride, m.p. 255°-258°
  3. customRemoval of solvent from the filtrate
  4. customgave a yellow oil which
  5. customcrystallized
  6. customRecrystallization from 25 ml of ethyl acetate and 10 ml of pentane

Sources & evidence

ORD record
ord-7d6649018b974eb4aa2d25ed87f51914
Source dataset
uspto-grants-1982_06
Patent number
US04335142

Reaction notes

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