Sodium Bicarbonate → HCID 178527290, compound

HRID 2219013Notes

Reaction equation

[NH2:1][C:2]1[C:11]([CH2:12][S:13]([C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=[CH:18][CH:17]=2)(=[O:15])=[O:14])=[CH:10][C:5]([O:6][CH2:7][CH2:8][OH:9])=[CH:4][C:3]=1[O:26][CH2:27][CH2:28][Cl:29].[N:30]([O-])=O.[Na+].C(=O)(O)[O-].[Na+]>C1COCC1.Cl.O>[Cl:29][CH2:28][CH2:27][O:26][C:3]1[CH:4]=[C:5]([O:6][CH2:7][CH2:8][OH:9])[CH:10]=[C:11]2[C:2]=1[NH:1][N:30]=[C:12]2[S:13]([C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][CH:17]=1)(=[O:14])=[O:15]

Participants

Conditions

Temperature: 3 °C

Procedure

A mixture of 2-[4-amino-3- (2-chloroethoxy)-5-(naphthalene-1-sulfonylmethyl)phenoxy]ethanol (1.22 g, 2.8 mmoles) in THF and 4M HCl was stirred, under nitrogen, at 3° C., treated dropwise with a solution of sodium nitrite (0.20 g, 2.94 mmoles) in H2O, poured into a cold solution of saturated sodium bicarbonate and extracted with EtOAc. The extracts were combined, dried over Na2SO4 and concentrated under vacuum to afford the title compound (1.18 g, 2.65 mmoles), identified by HNMR and mass spectral analyses.

Workup

extractionextracted with EtOAc
dry with materialdried over Na2SO4
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-e53a3b7fcab54cbcbe34acc2e9a6c9f9
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07414051B2

Reaction notes

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