Water → N-(4-hydroxy-3-(1-methyl-1H-tetrazol-5-ylthio)naphthalen-1-yl)thiophene-2-sulfonamide

HRID 1258390Notes

Reaction equation

HRID 1258390 reaction equation
[CH3:1][N:2]1[C:6]([S:7][C:8]2[C:17](=[O:18])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)/[C:10](=[N:19]/[S:20]([C:23]3[S:24][CH:25]=[CH:26][CH:27]=3)(=[O:22])=[O:21])/[CH:9]=2)=[N:5][N:4]=[N:3]1.S(S([O-])=O)([O-])=O.[Na+].[Na+].O>C(OCC)(=O)C>[OH:18][C:17]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([NH:19][S:20]([C:23]2[S:24][CH:25]=[CH:26][CH:27]=2)(=[O:22])=[O:21])=[CH:9][C:8]=1[S:7][C:6]1[N:2]([CH3:1])[N:3]=[N:4][N:5]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24489Sodium DithioniteHCID 46907997(NE)-N-[3-(1-methyltetrazol-5-yl)sulfanyl-4-oxonaphthalen-1-ylidene]thiophene-2-sulfonamide

Product 1

HCID 135895396N-(4-hydroxy-3-(1-methyl-1H-tetrazol-5-ylthio)naphthalen-1-yl)thiophene-2-sulfonamideYield 99.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

13 mg (E)-N-(3-(1-methyl-1H-tetrazol-5-ylthio)-4-oxonaphthalen-1(4H)-ylidene)thiophene-2-sulfonamide (13d) was dissolved in 50 ml ethyl acetate, to which was added 27 mg sodium hydrosulfite solid followed by 10 ml water. The mixture was shaken in a separation funnel until the yellow organic phase turned colorless. The organic phase was separated and washed with water and brine. Dried over Na2SO4, the organic phase was filtered and the filtrate was concentrated to dryness. The residue was dissolved in dichloromethylene and triturated with hexane. The precipitate was washed with dichloromethylene/hexane (1:1) affording the title compound 13 mg (99%) as a white solid, m.p.: 130° C. (dec.).

Workup

  1. customThe organic phase was separated
  2. washwashed with water and brine
  3. dry with materialDried over Na2SO4
  4. filtrationthe organic phase was filtered
  5. concentrationthe filtrate was concentrated to dryness
  6. dissolutionThe residue was dissolved in dichloromethylene
  7. customtriturated with hexane
  8. washThe precipitate was washed with dichloromethylene/hexane (1:1)

Sources & evidence

ORD record
ord-1dd3c199320d4a189f1346049e565bfd
Source dataset
uspto-grants-2013_06
Patent number
US08466157B2

Reaction notes

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