Hydrochloric Acid → HCID 20222658, compound

HRID 1248438Notes

Reaction equation

[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([C:13]([OH:15])=[O:14])=[C:7]2[OH:12].Cl[S:17]([C:20]1[CH:21]=[C:22]([S:28]([F:31])(=[O:30])=[O:29])[CH:23]=[CH:24][C:25]=1[O:26][CH3:27])(=[O:19])=[O:18].CN(C)C1C=CC=CC=1.Cl>CN(C)C(=O)C>[F:31][S:28]([C:22]1[CH:23]=[CH:24][C:25]([O:26][CH3:27])=[C:20]([S:17]([NH:1][C:2]2[CH:11]=[CH:10][CH:9]=[C:8]3[C:3]=2[CH:4]=[CH:5][C:6]([C:13]([OH:15])=[O:14])=[C:7]3[OH:12])(=[O:18])=[O:19])[CH:21]=1)(=[O:29])=[O:30]

Participants

Conditions

Temperature: 22 °C

Procedure

5-Amino-1-hydroxy-2-naphthoic acid (10.2 g, 50 mmol) and 3-chlorosulfonyl-4-methoxybenzenesulfonylfluoride (14.4 g, 50 mmol) as prepared as in 1A were suspended in N,N-dimethylacetamide (100 ml). N,N-Dimethylaniline (15.1 g, 125 mmol) was added, the mixture was stirred at room temperature (22° C.) for 16 hours, and was then poured into ice water (750 ml) acidified with concentrated hydrochloric acid (25 ml). The mixture was extracted with three portions of ethyl acetate (500 ml each). The combined extracts were dried over anhydrous magnesium sulfate, the salts were removed by filtration, and the filtrate was decolorized with acidic alumina. The alumina was separated and the solvent was removed under reduced pressure to yield 8.3 g, (36.4%) of product.

Workup

extractionThe mixture was extracted with three portions of ethyl acetate (500 ml each)
dry with materialThe combined extracts were dried over anhydrous magnesium sulfate
customthe salts were removed by filtration
customThe alumina was separated
customthe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-48234cd438eb4e96b1f226316454a7c3
Source dataset: uspto-grants-1985_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04524122

Reaction notes

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