Methyl p-toluenesulfonate → HCID 86760673, compound

HRID 2224002Notes

Reaction equation

HRID 2224002 reaction equation
[CH3:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([C:11]3[O:12][C:13]4[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=4[N:15]=3)[CH:8]=[CH:7][C:5]=2[N:6]=1.[S:20]([C:25]1[CH:31]=[CH:30][C:28]([CH3:29])=[CH:27][CH:26]=1)([O:23][CH3:24])(=[O:22])=[O:21]>>[S:20]([C:25]1[CH:31]=[CH:30][C:28]([CH3:29])=[CH:27][CH:26]=1)([O-:23])(=[O:22])=[O:21].[CH3:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([C:11]3[O:12][C:13]4[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=4[N:15]=3)[CH:8]=[CH:7][C:5]=2[N+:6]=1[CH3:24]

Participants

3

Reactant 2

HCID 6645Methyl p-toluenesulfonateHCID 17953506HCID 17953506, compound

Product 1

HCID 86760673HCID 86760673, compound

Procedure

2-methyl-6-(benzoxazol-2-yl)-benzothiazole (50 mg, 0.22 mmol) was stirred for 3 h at 90° C. in m excess of melted methyl tosylate (900 mg, 4.78 mmol). After being allowed to cool to room temperature, the product was precipitated by addition of acetone and collected by filtration. The precipitate was washed with acetone and allowed to dry over night. This gave the product as light brown crystals. Yield: 56 mg, 56%. 1H NMR (DMSO): δ 2.27 (s, 3H, CH3), 3.21 (s, 3H, —CH3), 4.24 (s, 3H, —CH3), 7.09 (d, J=8, 2H, ArH), 7.47 (M, 4H, ArH), 7.88 (t, J=8.8, 2H, ArH), 8.49 (d, J=8.8, 1H, ArH), 8.64 (d, J=8.8, 1H, ArH), 9.32 (a, 1H, ArH). HR-FAB-MS m/z Found: 281.078 C16H13N2OS (M+): requires M, 281.075.

Workup

  1. customthe product was precipitated by addition of acetone
  2. filtrationcollected by filtration
  3. washThe precipitate was washed with acetone
  4. customto dry over night

Sources & evidence

ORD record
ord-97f541f9805a4c67b8ed51b683e5daaa
Source dataset
uspto-grants-2008_05
Patent number
US07378240B2

Reaction notes

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