Sodium sulfide nonahydrate → HCID 178507594, compound

HRID 499720Notes

Reaction equation

HRID 499720 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[NH:11][C:12]1[S:13][C:14](=[CH:18][C:19]2[CH:20]=[C:21]3[C:26](=[CH:27][CH:28]=2)[N:25]=[CH:24][CH:23]=[CH:22]3)[C:15](=[O:17])[N:16]=1.O.O.O.O.O.O.O.O.O.[S-2].[Na+].[Na+]>CCO>[NH2:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([NH:11][C:12]2[S:13][C:14](=[CH:18][C:19]3[CH:20]=[C:21]4[C:26](=[CH:27][CH:28]=3)[N:25]=[CH:24][CH:23]=[CH:22]4)[C:15](=[O:17])[N:16]=2)[CH:4]=1

Participants

4

Reactant 2

HCID 73972Sodium sulfide nonahydrateHCID 178518027HCID 178518027, compound

Product 1

HCID 178507594HCID 178507594, compoundYield 20.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-(2-chloro-5-nitro-phenylamino)-5-quinolin-6-ylmethylene-thiazol4-one (100 mg, 0.42 mmol) and sodium sulfide nonahydrate (350 mg, 1-66 mmol) in 4 ml of EtOH was heated by microwave (SmithSynthesizer-Personal Chemistry) at 130 for 2 hours. The reaction mixture was cooled to room temperature and concentrated by vacuum distillation, then water was added and neutralized with aqueous ammonium chloride. Generated solid was collected by filtration and washed with water, followed by desiccation in vacuo to afford the title product (33 mg, 0.086 mmol). 1H NMR(DMSO-d6) δ 12.63 (s, 1H) 8.94 (m, 1H) 8.47 (d, 1H) 4.16 (s, 1H) 8.10 (d, 1H) 7.87 (dd, 1H) 7.84 (s, 1H) 7.56 (dd, 1H) 7.12 (d, 1H) 6.40 (d, 1H) 6.38 (s, 1H) 5.37 (s, 2H).:LC/MS: m/z 381 (M+1)

Workup

  1. temperaturewas heated by microwave (SmithSynthesizer-Personal Chemistry) at 130 for 2 hours
  2. concentrationconcentrated by vacuum distillation
  3. additionwater was added
  4. filtrationwas collected by filtration
  5. washwashed with water

Sources & evidence

ORD record
ord-19e8ae4235b84bd196cc9096ee7b5ee9
Source dataset
uspto-grants-2010_08
Patent number
US07767701B2

Reaction notes

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