Triethylamine → HCID 86602885, compound

HRID 1819381Notes

Reaction equation

HRID 1819381 reaction equation
[Cl:1][C:2]1[C:7]([N:8]([CH3:10])[CH3:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:11][OH:12].C(N(CC)CC)C.[CH3:20][S:21](Cl)(=[O:23])=[O:22].CN(C1C=CC=CN=1)C>ClCCl>[Cl:1][C:2]1[C:7]([N:8]([CH3:9])[CH3:10])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:11][O:12][S:21]([CH3:20])(=[O:23])=[O:22]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 31297Methanesulfonyl chlorideHCID 57885763HCID 57885763, compound

Product 1

HCID 86602885HCID 86602885, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

(2-Chloro-3-dimethylamino-phenyl)-methanol (0.50 g, 2.69 mmol) was placed in a round bottomed flask with dichloromethane (10 mL) and cooled to 0° C. Triethylamine (0.68 g, 6.73 mmol), methanesulfonylchloride (0.23 mL, 2.97 mmol), and dimethylaminopyridine (0.02 g) were added and the reaction was allowed to warm and stir at rt over 3 h. The reaction was diluted with dichloromethane (20 mL) and washed with 1N Hydrochloric acid (10 mL), 10% aqueous sodium bicarbonate (10 mL), and water (10 mL). The organics were dried (MgSO4) and concentrated to afford methanesulfonic acid 2-chloro-3-dimethylamino-benzyl ester.

Workup

  1. temperatureto warm
  2. washwashed with 1N Hydrochloric acid (10 mL), 10% aqueous sodium bicarbonate (10 mL), and water (10 mL)
  3. dry with materialThe organics were dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-cdab7aabeb2c48c7988acb5b2e170b2c
Source dataset
uspto-grants-2009_10
Patent number
US07601714B2

Reaction notes

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