4-Acetylamino-naphthalene-1-sulfonic acid thiazol-2-ylamide → 4-Amino-naphthalene-1-sulfonic acid thiazol-2-ylamide

HRID 452936Notes

Reaction equation

[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[NH:6][S:7]([C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([NH:20]C(=O)C)=[CH:12][CH:11]=1)(=[O:9])=[O:8]>C[O-].[Na+]>[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[NH:6][S:7]([C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([NH2:20])=[CH:12][CH:11]=1)(=[O:9])=[O:8]

Participants

Conditions

Temperature: 70 °C

Procedure

N-[4-(Thiazol-2-ylsulfamoyl)-naphthalen-1-yl]-acetamide (0.48 g, 1.38 mmol) was dissolved in 0.5 M NaOMe (20 ml) and heated at 70° C. for 16 h. After the solvents were evaporated, a 2:1 EtOH:H2O mixture (6 ml) and a few drops of AcOH were added. While stirring the mixture, a precipitate formed which was filtered and dried under vacuum to give 4-amino-naphthalene-1-sulfonic acid thiazol-2-ylamide (0.31 g, 73%). LC/MS (10-99% CH3CN), M/Z: M+1 obs=306.0; tR=2.04 min.

Workup

customAfter the solvents were evaporated
additiona 2:1 EtOH:H2O mixture (6 ml) and a few drops of AcOH were added
customa precipitate formed which
filtrationwas filtered
customdried under vacuum

Sources & evidence

ORD record: ord-d7a0e9b23ca6405daa5c5a72783079ba
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08492403B2

Reaction notes

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