Hydrochloric Acid → HCID 67595026, compound

HRID 865306Notes

Reaction equation

HRID 865306 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:12])[CH2:7][S:8][CH2:9]2)=[CH:4][CH:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[F:23][C:24]([F:33])([F:32])[C:25](C1NC=CN=1)=[O:26].Cl>O1CCCC1>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:12])[CH:7]([C:25](=[O:26])[C:24]([F:33])([F:32])[F:23])[S:8][CH2:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 5654362,2,2-Trifluoro-1-(1H-imidazol-2-yl)ethanoneHCID 2724254Sodium bis(trimethylsilyl)amideHCID 22394204HCID 22394204, compound

Product 1

HCID 67595026HCID 67595026, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

7-Chloroisothiochroman-4-one from Step 3 (0.3 g, 1.5 mmol) was dissolved in tetrahydrofuran (15 mL) and cooled to -78° C. A solution of sodium bistrimethylsilyl amide (1.5 mL of a 1.0M tetrahydrofuran solution) was added and the reaction stirred for 0.5 hours at -78° C. Trifluoroacetyl imidazole (0.21 mL, 1.8 mmol) was added and the reaction was warmed to room temperature and stirred under a nitrogen atmosphere for 16 hours. 1N Hydrochloric acid (100 mL) was added to the reaction followed by extraction with ether (150 mL). The organics were washed with brine (75 mL), dried over MgSO4 and concentrated in vacuo. The resulting yellow oil was used in the next step without further purification.

Workup

  1. temperaturethe reaction was warmed to room temperature
  2. stirringstirred under a nitrogen atmosphere for 16 hours
  3. extractionfollowed by extraction with ether (150 mL)
  4. washThe organics were washed with brine (75 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe resulting yellow oil was used in the next step without further purification

Sources & evidence

ORD record
ord-f1a09d8bb4fb4ff58a34adc267418e3b
Source dataset
uspto-grants-1996_10
Patent number
US05565482

Reaction notes

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