4-(Propan-2-yl)benzene-1-sulfonyl chloride → HCID 67023981, compound

HRID 450722Notes

Reaction equation

HRID 450722 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]([CH2:12][NH:13][C:14](=[O:17])[CH2:15][CH3:16])[CH2:7][CH2:6][CH2:5]2.[CH:18]([C:21]1[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1)([CH3:20])[CH3:19]>N1C=CC=CC=1>[CH:18]([C:21]1[CH:26]=[CH:25][C:24]([S:27]([NH:1][C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[CH:8]([CH2:12][NH:13][C:14](=[O:17])[CH2:15][CH3:16])[CH2:7][CH2:6][CH2:5]3)(=[O:29])=[O:28])=[CH:23][CH:22]=1)([CH3:20])[CH3:19]

Participants

4

Reactant 2

HCID 27348824-(Propan-2-yl)benzene-1-sulfonyl chlorideHCID 67023964HCID 67023964, compound

Product 1

HCID 67023981HCID 67023981, compoundYield 101.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of N-(6-amino-1,2,3,4-tetrahydro-naphthalen-1-ylmethyl)-propionamide (290 mg, 1.26 mmol) in pyridine (10 ml) at 0° C. 4-isopropyl-benzenesulfonyl chloride (280 mg, 1.26 mmol) was added. The mixture was stirred at 0° C. for 1 h and 16 h at room temperature. After evaporation under reduced pressure the obtained residue was partitioned between ethyl acetate and saturated aqueous NaHCO3. The organic layer was washed twice with saturated aqueous NaHCO3, dried over MgSO4, filtered and the solvent evaporated under reduced pressure to give the product as a brown resin (530 mg, 100%).

Workup

  1. customat 0° C
  2. customAfter evaporation under reduced pressure the obtained residue
  3. customwas partitioned between ethyl acetate and saturated aqueous NaHCO3
  4. washThe organic layer was washed twice with saturated aqueous NaHCO3
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-29384dd629804da3a20155c7185548b5
Source dataset
uspto-grants-2013_07
Patent number
US08486984B2

Reaction notes

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