4-(2-Chloroethyl)morpholine → 7-(2-Morpholinoethoxy)naphthalene-2-sulfonic acid

HRID 528805Notes

Reaction equation

HRID 528805 reaction equation
[O-:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([S:12]([O-:15])(=[O:14])=[O:13])=[CH:9]2)=[CH:4][CH:3]=1.[Na+].[Na+].Cl[CH2:19][CH2:20][N:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1>>[O:24]1[CH2:25][CH2:26][N:21]([CH2:20][CH2:19][O:1][C:2]2[CH:11]=[C:10]3[C:5]([CH:6]=[CH:7][C:8]([S:12]([OH:15])(=[O:13])=[O:14])=[CH:9]3)=[CH:4][CH:3]=2)[CH2:22][CH2:23]1

Participants

3

Reactant 2

HCID 767274-(2-Chloroethyl)morpholineHCID 86718866Sodium 7-oxidonaphthalene-2-sulfonate

Product 1

HCID 867188657-(2-Morpholinoethoxy)naphthalene-2-sulfonic acidYield 45%

Procedure

Following a procedure analogous to that for the synthesis of Intermediate 26B, sodium 7-oxidonaphthalene-2-sulfonate (Pfaltz and Bauer, 200 mg, 0.75 mmol) and 4-(2-chloroethyl)morpholine (223 g, 1.49 mmol) were converted to the title compound (113 mg, 45%). 1H NMR (DMSO-d6) δ 9.90 (br s, 1H), 8.10 (s, 1H), 7.86 (d, J=8.8 Hz, 1H), 7.80 (d, J=8.4 Hz, 1H), 7.58 (dd, J=8.1, 1.3 Hz, 1H), 7.49 (d, J=1.8 Hz, 1H), 7.24 (dd, J=8.7, 2.3 Hz, 1H), 4.48 (br s, 2H), 3.99 (br s, 2H), 3.65 (br s, 4H), 3.26 (br s, 4H); MS (ESI+) m/z 336.3 (M+H)+.

Sources & evidence

ORD record
ord-6e71287d6eb34fcaa5a67a2591ec429c
Source dataset
uspto-grants-2016_05
Patent number
US09346795B2

Reaction notes

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