Benzyl Alcohol → HCID 15524161, compound

HRID 369490Notes

Reaction equation

HRID 369490 reaction equation
[Cl:1][CH2:2][CH2:3][N:4]([CH2:16][CH2:17][Cl:18])[C:5]1[C:13]([CH3:14])=[CH:12][C:11]([CH3:15])=[CH:10][C:6]=1[C:7]([OH:9])=[O:8].[CH2:19](O)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.ClCCl>[Cl:1][CH2:2][CH2:3][N:4]([CH2:16][CH2:17][Cl:18])[C:5]1[C:13]([CH3:14])=[CH:12][C:11]([CH3:15])=[CH:10][C:6]=1[C:7]([O:9][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:8]

Participants

6

Reactant 3

HCID 244Benzyl AlcoholHCID 10868DicyclohexylcarbodiimideHCID 9817460HCID 9817460, compound

Product 1

HCID 15524161HCID 15524161, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

2-Bis(2'-chloroethyl)amino-3,5-dimethylbenzoic acid (1.0 g, 3.45 mmol), benzyl alcohol (0.75 g, 6.90 mmol), 1,3-dicyclohexylcarbodiimide (0.82 g, 3.975 mmol), and 4-dimethylaminopyridine (0.50 g, 4.03 mmol) were dissolved in 25 mL dichloromethane at room temperature to form a reaction mixture. The mixture was stirred for 17 hours, diluted with hexanes (10 mL), cooled in the freezer for 20 minutes, and then filtered, It was then concentrated and then subjected to flash chromatographic purification (silica gel, 5% to 10% ethyl acetate in hexanes) to afford the product as a white oil (1.20 g, 92%). 1H NMR (300 MHz, CDCl3): 7.4 (m, 5H), 7.33 (d, J=2.1 Hz, 1H), 7.17 (d, J=2.1 Hz, 1H), 5.32 (s, 2H), 3.46 (m, 4H), 3.30 (br m, 4H), 2.33 (s, 3H), 2.29 (s, 3H). ESMS calcd (C20H23Cl2NO3): 379.1; found: 380.2 (M+H)+.

Workup

  1. customto form a reaction mixture
  2. temperaturecooled in the freezer for 20 minutes
  3. filtrationfiltered
  4. concentrationIt was then concentrated
  5. customsubjected to flash chromatographic purification (silica gel, 5% to 10% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-378f614caf6c4251b176543dec3cccbe
Source dataset
uspto-grants-2000_10
Patent number
US06137003

Reaction notes

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