4-Toluenesulfonyl chloride → HCID 69809888, compound

HRID 2384524Notes

Reaction equation

HRID 2384524 reaction equation
O[CH2:2][CH2:3][NH:4][C:5]([C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=1)=[O:6].C1(C)C=CC(S(Cl)(=O)=O)=CC=1.C(N(CC)CC)C>ClCCCl>[N:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:15]=[CH:16][CH:7]=1.[O:6]1[CH2:2][CH2:3][N:4]=[CH:5]1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 4319814HCID 4319814, compound

Product 1

HCID 69809888HCID 69809888, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Conditions

Temperature
-5 °C

Procedure

N-(2-hydroxyethyl)quinoline-2-carboxamide was dissolved in DCE (40 mL) in an oven dried 100 mL pear bottomed flask. To a 250 mL 3 necked round bottomed flask was fitted a water condenser, and a magnetic stir bar was added. p-Toluene sulfonyl chloride (2.2288 g, 11.65 mmol) and N,N-dimethylaminopyridine (95.4 mg, 0.78 mmol) were added to the reaction flask. The flask was placed under N2 atmosphere. DCE (30 mL) was added to the reaction flask and cooled to −5° C. The reaction flask was charged with triethylamine (5.50 mL, 39 mmol). The reaction mixture was stirred for 10 min and allowed react according to the formula

Workup

  1. customdried 100 mL pear bottomed flask
  2. customTo a 250 mL 3 necked round bottomed flask was fitted a water condenser, and a magnetic stir bar
  3. additionwas added
  4. customallowed react

Sources & evidence

ORD record
ord-3a454c11b4ee4c2eb8f12424ee078724
Source dataset
uspto-grants-2012_09
Patent number
US08263774B2

Reaction notes

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