Triethylamine → HCID 69036283, compound

HRID 1820792Notes

Reaction equation

HRID 1820792 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:8]([S:11]([OH:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C(N(CC)CC)C.[Cl:21][CH2:22][CH2:23][CH2:24]I>CN(C=O)C>[Cl:21][CH2:22][CH2:23][CH2:24][S:11]([C:8]1[CH:9]=[CH:10][C:2]([OH:1])=[C:3]([CH:7]=1)[C:4]([OH:6])=[O:5])(=[O:13])=[O:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 813631-Chloro-3-iodopropaneHCID 2489022-hydroxy-5-sulfinobenzoic acid

Product 1

HCID 69036283HCID 69036283, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

To 16.7 mmol 2-hydroxy-5-sulfino-benzoic acid and 41.7 mmol triethylamine in 40 ml DMF was added 18.3 mmol 1-chloro-3-iodopropane, and the mixture heated at 40° C. for 1 h. The mixture was then cooled to room temperature and concentrated in vacuo. The residue was chromatographed on silica gel (eluant: dichloromethane/methanol/acetic acid gradient) to afford the title compound. MS (m/e): 279.1 ([{37Cl}M−H]−, 33%), 277.0 ([{35Cl}M−H]−, 100%)

Workup

  1. temperatureThe mixture was then cooled to room temperature
  2. concentrationconcentrated in vacuo
  3. customThe residue was chromatographed on silica gel (eluant: dichloromethane/methanol/acetic acid gradient)

Sources & evidence

ORD record
ord-286fb2e2f50d4d7da3b7eea445f1a81d
Source dataset
uspto-grants-2009_10
Patent number
US07605163B2

Reaction notes

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