Pyridine → (NE)-N-[3-(1-methyltetrazol-5-yl)sulfanyl-4-oxonaphthalen-1-ylidene]-4-phenylbenzenesulfonamide

HRID 1258399Notes

Reaction equation

HRID 1258399 reaction equation
Cl[C:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)/[C:4](=[N:13]/[S:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:19][CH:18]=2)(=[O:16])=[O:15])/[CH:3]=1.[CH3:29][N:30]1[C:34]([SH:35])=[N:33][N:32]=[N:31]1.N1C=CC=CC=1>C1COCC1>[CH3:29][N:30]1[C:34]([S:35][C:2]2[C:11](=[O:12])[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)/[C:4](=[N:13]/[S:14]([C:17]3[CH:22]=[CH:21][C:20]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[CH:19][CH:18]=3)(=[O:16])=[O:15])/[CH:3]=2)=[N:33][N:32]=[N:31]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 58398230(NE)-N-(3-chloro-4-oxonaphthalen-1-ylidene)-4-phenylbenzenesulfonamideHCID 178482017HCID 178482017, compound

Product 1

HCID 46908285(NE)-N-[3-(1-methyltetrazol-5-yl)sulfanyl-4-oxonaphthalen-1-ylidene]-4-phenylbenzenesulfonamideYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

81.6 mg 12b was dissolved in 2 ml THF. 1 ml THF solution containing 1 eq. 1-methyl-tetrazole-5-thiol and 1 eq. pyridine was added. The mixture was shaken for 30 min. The organic solvent was removed by V-10 (biotage). The residue was suspended in 10 ml water and sonicated thoroughly. The insoluble was filtered and washed with water. The solid was dried over air affording 96.5 mg (99.0%) title compound 13x.

Workup

  1. customThe organic solvent was removed by V-10 (biotage)
  2. customsonicated thoroughly
  3. filtrationThe insoluble was filtered
  4. washwashed with water
  5. customThe solid was dried over air

Sources & evidence

ORD record
ord-8764c6a0fd5945829a56eca87c73d2e7
Source dataset
uspto-grants-2013_06
Patent number
US08466157B2

Reaction notes

Loading…