Water → HCID 86640518, compound

HRID 1091677Notes

Reaction equation

HRID 1091677 reaction equation
[H-].[Na+].[F:3][C:4]([F:16])([F:15])[C:5]1[CH:10]=[CH:9][N:8]=[C:7]([CH2:11][C:12]([NH2:14])=[O:13])[N:6]=1.[N:17]([C:20]1[CH:33]=[CH:32][C:23]([O:24][CH2:25][CH2:26][N:27]2[CH:31]=[CH:30][N:29]=[CH:28]2)=[CH:22][CH:21]=1)=[C:18]=[S:19].O>C1COCC1>[N:27]1([CH2:26][CH2:25][O:24][C:23]2[CH:32]=[CH:33][C:20]([NH:17][C:18](=[S:19])[CH:11]([C:7]3[N:6]=[C:5]([C:4]([F:3])([F:15])[F:16])[CH:10]=[CH:9][N:8]=3)[C:12]([NH2:14])=[O:13])=[CH:21][CH:22]=2)[CH:31]=[CH:30][N:29]=[CH:28]1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 22641003HCID 22641003, compoundHCID 66593263HCID 66593263, compound

Product 1

HCID 86640518HCID 86640518, compoundYield 73.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Sodium hydride (0.531 g of a 60 wt % dispersion in oil, 13.3 mmol) was added in portions to a stirred solution of 2-(4-trifluoromethylpyrimidin-2-yl)acetamide (0.911 g; 4.43 mmol) in THF (20 mL) over 10 min. A solution of 1-[2-(4-isothiocyanatophenoxy)ethyl]-1H-imidazole (1.21 g; 4.92 mmol) in THF (10 mL) was then added over 15 min. The mixture was stirred at room temperature for a further 1 hr, and then water (1 mL) was added and the mixture was concentrated under reduced pressure. Water (75 mL) was added to the residue, the pH adjusted to 7 with 2N hydrochloric acid, and the mixture was extracted three times with EA. The combined EA extracts were washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure to give 3-{-4-[2-(1H-imidazol-1-yl)ethoxy]phenylamino}-3-thioxo-2-(4-trifluoromethylpyrimidin-2-yl)propanamide (1.47 g) as an orange semi-solid.

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. additionWater (75 mL) was added to the residue
  3. extractionthe mixture was extracted three times with EA
  4. washThe combined EA extracts were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4514f924a11c4be2b6a90dd6bbb0c8cb
Source dataset
uspto-grants-2012_03
Patent number
US08129396B2

Reaction notes

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