Triethylamine → HCID 25188596, compound

HRID 1644758Notes

Reaction equation

HRID 1644758 reaction equation
[OH:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[C:4]([NH:6][C:7]1[S:8][CH:9]=[CH:10][N:11]=1)=[O:5].C(N(CC)CC)C.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>ClCCl>[CH3:23][S:24]([O:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[C:4](=[O:5])[NH:6][C:7]1[S:8][CH:9]=[CH:10][N:11]=1)(=[O:26])=[O:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 578639Benzamide, 2-hydroxy-N-2-thiazolyl-

Product 1

HCID 25188596HCID 25188596, compoundYield 78.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-hydroxy-N-1,3-thiazol-2-ylbenzamide (502, 267.1 mg, 1.21 mmol) was placed into a 10 mL round bottom flask equipped with a stirbar and a septum with a dry nitrogen inlet. Dichloromethane (5.0 mL) and triethylamine (500 μL, 3.59 mmol) were added to form a light pink solution. Methanesulfonyl chloride (100 μL, 1.3 mmol) in dichloromethane (ca. 1.0 mL) was added dropwise to the stirring solution over ca. 30 seconds, and the reaction was stirred at room temperature for ca. 20 minutes before being quenched into saturated NaHCO3, and extracted with dichloromethane. The combined organics were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. The crude product was recrystallized from hexanes/ethyl acetate to yield (284 mg, 78%) of 11 as a colorless crystalline solid. Example 11 (2-thiazol-2-ylcarbamoyl)phenyl methanesulfonate) has the empirical formula C11H10N2O4S and a molecular weight of 298.34.

Workup

  1. customequipped with a stirbar
  2. customto form a light pink solution
  3. custombefore being quenched into saturated NaHCO3
  4. extractionextracted with dichloromethane
  5. washThe combined organics were washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude product was recrystallized from hexanes/ethyl acetate

Sources & evidence

ORD record
ord-949772bae76942e694b82fa28f14054c
Source dataset
uspto-grants-2012_02
Patent number
US08124632B2

Reaction notes

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