2-Dimethylaminopyridine → HCID 67206214, compound

HRID 384531Notes

Reaction equation

HRID 384531 reaction equation
[CH3:1][C:2]1[CH:20]=[CH:19][C:5]2[N:6]=[C:7]([O:9][C:10]3[CH:15]=[CH:14][C:13]([CH2:16][CH2:17]O)=[CH:12][CH:11]=3)[S:8][C:4]=2[CH:3]=1.CN(C1C=CC=CN=1)C.CCN(C(C)C)C(C)C.[CH3:39][S:40](Cl)(=[O:42])=[O:41]>C(Cl)Cl>[CH3:39][S:40]([CH2:17][CH2:16][C:13]1[CH:14]=[CH:15][C:10]([O:9][C:7]2[S:8][C:4]3[CH:3]=[C:2]([CH3:1])[CH:20]=[CH:19][C:5]=3[N:6]=2)=[CH:11][CH:12]=1)(=[O:42])=[O:41]

Participants

6

Reactant 4

HCID 218852-DimethylaminopyridineHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 672056662-[4-(6-Methyl-benzothiazol-2-yloxy)-phenyl]-ethanol

Product 1

HCID 67206214HCID 67206214, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-[4-(6-methyl-benzothiazol-2-yloxy)-phenyl]-ethanol (6.8 g, 23.8 mmol) and dimethylaminopyridine (290 mg, 2.4 mmol) in CH2Cl2 (80 mL) was added (i-Pr)2NEt (4.9 g, 28.6 mmol) followed by the addition of methanesulfonyl chloride (2.2 mL, 28.6 mmol) at 0° C. The reaction was warmed to rt and stirred for 15 min. The reaction was washed with satd. aq. Na2CO3 (75 mL), 5% aq. H2SO4 (75 mL) and brine. The organic layer was dried (Na2SO4), filtered and concentrated to afford the title compound (7.3 g, 85%). 1H NMR (500 MHz, CDCl3): 7.61 (d, J=8.3 Hz, 1H), 7.47 (s, 1H), 7.36-7.29 (m, 4H), 7.20 (dd, J=8.3, 1.2 Hz, 1H), 4.45 (t, J=6.8 Hz, 2H), 3.10 (t, J=6.8 Hz, 2H), 2.91 (s, 3H), 2.44 (s, 3H).

Workup

  1. washThe reaction was washed with satd
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3d025c2b5ba9473ab64b6e6e7ebecfa3
Source dataset
uspto-grants-2013_02
Patent number
US08367719B2

Reaction notes

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