4-(Propan-2-yl)benzene-1-sulfonyl chloride → HCID 67023968, compound

HRID 450732Notes

Reaction equation

HRID 450732 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH:5]([CH2:11][NH:12][C:13](=[O:16])[CH2:14][CH3:15])[CH2:6]2.[CH:17]([C:20]1[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1)([CH3:19])[CH3:18]>N1C=CC=CC=1.ClCCl>[CH:17]([C:20]1[CH:25]=[CH:24][C:23]([S:26]([NH:1][C:2]2[CH:10]=[CH:9][CH:8]=[C:7]3[C:3]=2[CH2:4][CH:5]([CH2:11][NH:12][C:13](=[O:16])[CH2:14][CH3:15])[CH2:6]3)(=[O:28])=[O:27])=[CH:22][CH:21]=1)([CH3:19])[CH3:18]

Participants

4

Reactant 2

HCID 27348824-(Propan-2-yl)benzene-1-sulfonyl chlorideHCID 67024079HCID 67024079, compound

Product 1

HCID 67023968HCID 67023968, compoundYield 101.4%

Reagents, catalysts & solvents 1

HCID 21875418Pyridine methylene chlorideSolvent

Conditions

Temperature
5 °C

Procedure

N-(4-Amino-indan-2-ylmethyl)-propionamide (0.51 g, 2.34 mmol) was dissolved in pyridine-dichloromethane (1:2, 30 mL) and cooled to 5° C. 4-Isopropylbenzenesulfonyl chloride (0.54 g, 2.47 mmol) was added and the solution stirred at 5° C. for 3 h. Solution was evaporated, partitioned between ethyl acetate and water, and the organic phase separated and dried over MgSO4. The filtered solution was concentrated to give the product as a brown oil (0.95 g, 100%).

Workup

  1. customSolution was evaporated
  2. custompartitioned between ethyl acetate and water
  3. customthe organic phase separated
  4. dry with materialdried over MgSO4
  5. concentrationThe filtered solution was concentrated

Sources & evidence

ORD record
ord-c23079da3bc84d0384501c2a412209fa
Source dataset
uspto-grants-2013_07
Patent number
US08486984B2

Reaction notes

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