Triethylamine → 2-(5-Methyl-2-phenyloxazol-4-yl)ethyl 4-methylbenzenesulfonate

HRID 2121692Notes

Reaction equation

HRID 2121692 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][OH:15].C(N([CH2:21][CH3:22])CC)C.[C:23]1(C)[C:24]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:26]=C[CH:28]=1>ClCCl.CN(C)C1C=CN=CC=1>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][O:15][S:29]([C:24]1[CH:25]=[CH:26][C:21]([CH3:22])=[CH:28][CH:23]=1)(=[O:31])=[O:30]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 8623o-Toluenesulfonyl chlorideHCID 7255852-(5-Methyl-2-phenyl-4-oxazolyl)ethanol

Product 1

HCID 120517392-(5-Methyl-2-phenyloxazol-4-yl)ethyl 4-methylbenzenesulfonate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(5-Methyl-2-phenyl-oxazol-4-yl)-ethanol (12.5 g, 61 mmol) in dichloromethane (200 mL) at −20° C. under N2 atmophere was added triethylamine (26 mL, 184 mmol) and catalytic amount of 4-dimethylamino pyridine (50 mg). This solution was then treated with toluenesulfonyl chloride (14.1 g, 73.8 mmol) and the reaction was allowed to equilibrate to 23° C. over 16 hours. Reaction was washed with water, 5% Na2CO3, saturated NH4Cl, and brine. Solvent was removed in vacuo and crude tosylate 1 (21.3 g) was carried on to the next step without further purification. M+1=358.2

Workup

  1. customReaction
  2. washwas washed with water, 5% Na2CO3, saturated NH4Cl, and brine
  3. customSolvent was removed in vacuo and crude tosylate 1 (21.3 g)
  4. customwas carried on to the next step without further purification

Sources & evidence

ORD record
ord-ecaa475c5d444bfab22e4eead022bb19
Source dataset
uspto-grants-2004_02
Patent number
US06696474B2

Reaction notes

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