7-Iodonaphthalene-2-sulfonamide → 8-(2-Morpholinoethoxy)naphthalene-2-sulfonamide

HRID 528803Notes

Reaction equation

HRID 528803 reaction equation
I[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([S:12]([NH2:15])(=[O:14])=[O:13])=[CH:9]2)=[CH:4][CH:3]=1.[O:16]1[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][O:24]C2C=CC=C3C=2C=C(S(O)(=O)=O)C=C3)[CH2:18][CH2:17]1>>[O:16]1[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][O:24][C:11]2[CH:2]=[CH:3][CH:4]=[C:5]3[C:10]=2[CH:9]=[C:8]([S:12]([NH2:15])(=[O:14])=[O:13])[CH:7]=[CH:6]3)[CH2:18][CH2:17]1

Participants

3

Reactant 2

HCID 710607367-Iodonaphthalene-2-sulfonamideHCID 867188638-(2-Morpholinoethoxy)naphthalene-2-sulfonic acid

Product 1

HCID 710606938-(2-Morpholinoethoxy)naphthalene-2-sulfonamideYield 27%

Procedure

Following a procedure analogous to that for the synthesis of Intermediate 11, 8-(2-morpholinoethoxy)naphthalene-2-sulfonic acid (100 mg, 0.30 mmol) was converted to the title compound (27 mg, 27%). 1H NMR (CD3OD) δ 8.82 (d, J=1.8 Hz, 1H), 8.05-8.01 (m, 1H), 7.99-7.94 (m, 1H), 7.63-7.60 (m, 2H), 7.16 (dd, J=5.3, 3.3 Hz, 1H), 4.70-4.65 (m, 2H), 4.00 (t, J=4.7 Hz, 4H), 3.79-3.74 (m, 2H), 3.49 (d, J=4.2 Hz, 2H), 3.33 (ddd, J=3.2, 1.8, 1.7 Hz, 2H); MS(ESI−) m/z 335.3 (M−H)−.

Sources & evidence

ORD record
ord-3e9f53612bc1432eabdb4d1db7922ddc
Source dataset
uspto-grants-2016_05
Patent number
US09346795B2

Reaction notes

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