Sodium Sulfide → HCID 58710059, compound

HRID 2375886Notes

Reaction equation

HRID 2375886 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[C:12]1[S:16][CH:15]=[N:14][CH:13]=1.[S-2].[Na+].[Na+]>CN1CCCC1=O>[N+:9]([C:6]1[CH:7]=[CH:8][C:3]([OH:2])=[C:4]([C:12]2[S:16][CH:15]=[N:14][CH:13]=2)[CH:5]=1)([O-:11])=[O:10]

Participants

4

Reactant 2

HCID 14804Sodium SulfideHCID 58709908HCID 58709908, compound

Product 1

HCID 58710059HCID 58710059, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 5-(2-methoxy-5-nitrophenyl)thiazole (156 mg, 0.660 mmol) and anhydrous sodium sulfide (309 mg, 3.96 mmol) in N-methylpyrrolidinone (2 mL) was heated at 160° C. for 2 h. After cooling to rt, the solvent was removed in vacuo, and the residue was partitioned between water (5 mL) and dichloromethane (20 mL). The organic phase was separated, dried over MgSO4, and purified by silica gel chromatography (3% MeOH in dichloromethane) to afford the title compound. 1H-NMR (CDCl3, 400 MHz): δ=7.18 (d, J=9.2 Hz, 1H), 8.08 (dd, J=1.6, 9.2 Hz, 1H), 8.45 (s, 1H), 8.52 (d, J=2.4 Hz, 1H), 8.86 (s, 1H), 11.95 (s, br, 1H). MS (ES+): m/z 223.14 [MH+]. HPLC: tR=2.68 min (ZQ2000, polar—5 min).

Workup

  1. temperatureAfter cooling to rt
  2. customthe solvent was removed in vacuo
  3. customthe residue was partitioned between water (5 mL) and dichloromethane (20 mL)
  4. customThe organic phase was separated
  5. dry with materialdried over MgSO4
  6. custompurified by silica gel chromatography (3% MeOH in dichloromethane)

Sources & evidence

ORD record
ord-447b518400344f338811ed3bfcfd0b8d
Source dataset
uspto-grants-2008_12
Patent number
US07465726B2

Reaction notes

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