2-Phenyl-2,3-dihydrobenzo[1,4]oxathiin-6-ol → 5-Nitro-2-(2-phenyl-2,3-dihydrobenzo[1,4]oxathiin-6-yloxy)pyridine

HRID 1455035Notes

Reaction equation

HRID 1455035 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([O:10][C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[O:17][CH:16]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:15]C3)=[N:8][CH:9]=1)([O-:3])=[O:2].C1(C2C[S:37]C3C=C(O)C=CC=3O2)C=CC=CC=1>>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([O:10][C:11]2[CH:20]=[CH:19][C:18]3[O:17][CH:16]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH2:15][S:37][C:13]=3[CH:12]=2)=[N:8][CH:9]=1)([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 179784522-Phenyl-2,3-dihydrobenzo[1,4]oxathiin-6-olHCID 17978512Orm-10103

Product 1

HCID 179786105-Nitro-2-(2-phenyl-2,3-dihydrobenzo[1,4]oxathiin-6-yloxy)pyridine

Procedure

5-Nitro-2-(2-phenyl-2,3-dihydrobenzo[1,4]oxathiin-6-yloxy)pyridine was prepared as described for 5-nitro-2-(2-phenylchroman-6-yloxy)pyridine in Example 1(b) using 269 mg 2-phenyl-2,3-dihydrobenzo[1,4]oxathiin-6-ol. The product was recrystallised from ethanol. 1H NMR (400 MHz, CDCl3) δ: 9.07 (d, 1H, J 2.8 Hz), 8.47 (dd, 1H, J 9.1, 2.8 Hz), 7.43 (m, 4H), 7.37-7.41 (m, 1H), 7.02 (d, 1H, J 9.1 Hz), 6.99 (d, 1H, J 8.9 Hz), 6.95 (d, 1H, J 2.8 Hz), 6.82 (dd, 1H, J 8.9, 2.8 Hz), 5.21 (dd, 1H, J 9.7, 1.9 Hz), 3.31 (dd, 1H, 13.2, 9.7 Hz), 3.11 (dd, 1H, 13.2, 1.9 Hz).

Workup

  1. customThe product was recrystallised from ethanol

Sources & evidence

ORD record
ord-b0b1b6c7aaa14299b8a5414b91986be8
Source dataset
uspto-grants-2009_01
Patent number
US07482340B2

Reaction notes

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