Water → HCID 68851604, compound

HRID 1821008Notes

Reaction equation

HRID 1821008 reaction equation
[H-].[Na+].[CH3:3][CH:4]([SH:6])[CH3:5].C([C:9]1[CH:10]=[C:11]([C:16]([NH:18][NH:19][C:20](=[O:29])[C:21]2[CH:26]=[CH:25][C:24]([Br:27])=[CH:23][C:22]=2[CH3:28])=O)C=[CH:13][C:14]=1F)#N.O.[CH3:31][N:32](C=O)C>>[C:31]([C:14]1[CH:13]=[C:16]([NH:18][NH:19][C:20](=[O:29])[C:21]2[CH:26]=[CH:25][C:24]([Br:27])=[CH:23][C:22]=2[CH3:28])[CH:11]=[CH:10][C:9]=1[S:6][CH:4]([CH3:5])[CH3:3])#[N:32]

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 63642-PropanethiolHCID 24758Sodium hydrideHCID 68851621HCID 68851621, compound

Product 1

HCID 68851604HCID 68851604, compoundYield 44%

Conditions

Temperature
100 °C

Procedure

Sodium hydride (95%) (0.8 mmol, 0.025 g) was added to a solution of 2-propanethiol (0.8 mmol, 0.09 mL) in DMF (4 mL) in an oven dried high pressure tube. This reaction mixture was stirred for 10 minutes at room temperature after which N′-(3-cyano-4-fluorophenylcarbonyl)-4-bromo-2-methylbenzhydrazide (0.53 mmol, 0.2 g) was added. The reaction mixture was heated at 100° C. for 16 h, cooled to room temperature, and combined with water. The resulting precipitate was collected by filtration and washed with water to yield 0.1 g (44%) of the title compound. 1H NMR (500 MHZ, DMSO) δ 8.28 (s, 1H), 8.14 (d, J=8.0, 1H), 7.76 (d, J=8.2, H), 7.55 (s, 1H), 7.49 (d, J=7.8, 1H), 7.36 (d, J=8.0, 1H), 3.80-3.90 (m, 1H), 2.40 (s, 3H), 1.34 (d, J=6.2, 6H)

Workup

  1. customdried high pressure tube
  2. additionwas added
  3. temperaturecooled to room temperature
  4. filtrationThe resulting precipitate was collected by filtration
  5. washwashed with water

Sources & evidence

ORD record
ord-d724c523367a445c838f0d29192b5bd3
Source dataset
uspto-grants-2009_10
Patent number
US07605171B2

Reaction notes

Loading…