Water → HCID 58961237, compound

HRID 916623Notes

Reaction equation

HRID 916623 reaction equation
[H-].[Na+].[NH2:3][C:4]1[C:13]2[C:8](=[CH:9][C:10]([Cl:14])=[CH:11][CH:12]=2)[N:7]=[CH:6][CH:5]=1.[Cl:15][C:16]1[S:20][CH:19]=[N:18][N:17]=1.O.CN([CH:25]=[O:26])C>>[Cl:14][C:10]1[CH:9]=[C:8]2[C:13]([C:4]([NH:3][C:25]([C:19]3[S:20][C:16]([Cl:15])=[N:17][N:18]=3)=[O:26])=[CH:5][CH:6]=[N:7]2)=[CH:12][CH:11]=1

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 947117-Chloro-4-aminoquinolineHCID 129564682-Chloro-1,3,4-thiadiazole

Product 1

HCID 58961237HCID 58961237, compoundYield 60%

Conditions

Temperature
80 °C

Procedure

NaH (0.023 g, 0.58 mmol) was added in portions to a solution of 4-amino-7-chloro-quinoline (0.1 g, 0.56 mmol) in DMF (6 ml) at room temperature and the mixture was stirred for 20 min. 5-Chloro-[1,3,4]thiadiazole derivative (0.108 g, 0.56 mmol) was then added in one portion and the mixture heated at 80° C. (oil bath temperature) for 18 h. The reaction mixture was allowed to cool to room temperature and water (15 ml) was added. The precipitate was separated by filtration, washed with Et2O and dried to afford the product (0.08 g, 60% yield).

Workup

  1. temperatureto cool to room temperature
  2. customThe precipitate was separated by filtration
  3. washwashed with Et2O
  4. customdried

Sources & evidence

ORD record
ord-5f21aeb908974aae92e2e6f06e197dbf
Source dataset
uspto-grants-2007_09
Patent number
US07271179B2

Reaction notes

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