Acetic acid--water (1/1) → HCID 18005592, compound

HRID 989258Notes

Reaction equation

HRID 989258 reaction equation
[Si]([C:8]1[N:9]([S:23]([N:26]([CH3:28])[CH3:27])(=[O:25])=[O:24])[C:10]([CH:13]([C:15]2[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[CH:17][CH:16]=2)[OH:14])=[CH:11][N:12]=1)(C(C)(C)C)(C)C.CC(O)=O.O>C1COCC1.O>[C:21]([C:18]1[CH:17]=[CH:16][C:15]([CH:13]([OH:14])[C:10]2[N:9]([S:23]([N:26]([CH3:27])[CH3:28])(=[O:24])=[O:25])[CH:8]=[N:12][CH:11]=2)=[CH:20][CH:19]=1)#[N:22]

Participants

5

Reactant 2

HCID 21899381Acetic acid--water (1/1)HCID 70112805HCID 70112805, compound

Product 1

HCID 18005592HCID 18005592, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

The compound obtained in Step C (4 g, 9.5 mmol) is brought to solution in 40 ml of THF. A mixture of AcOH/H2O (7:3) (40 ml) is then added, and the whole is stirred at room temperature for 2 hours. The reaction mixture is then hydrolysed in a mixture of ice and H2O, extracted with AcOEt and washed with a saturated NaHCO3 solution, and then with a saturated NaCl solution, dried over MgSO4 and concentrated to dryness. The residual solid is then triturated in heptane, and the title product is obtained in the form of white crystals, 2.57 g, in a yield of 89%. IR: 3200 2700 ν(OH); 2230 ν(CN); 1390 and 1152 ν cm−1 (NSO2). NMR (CDCl3): 7.9, s, (1H); 7.75 and 7.55 2d, (4H); 6.55 s (1H); 6.15 d (1H); 3.25d(1H,OH); 3.0,s,(6H).

Workup

  1. additionis then added
  2. extractionextracted with AcOEt
  3. washwashed with a saturated NaHCO3 solution
  4. dry with materialwith a saturated NaCl solution, dried over MgSO4
  5. concentrationconcentrated to dryness
  6. customThe residual solid is then triturated in heptane

Sources & evidence

ORD record
ord-1eec9d51fbbd43f4b82e680127f63f33
Source dataset
uspto-grants-2003_10
Patent number
US06638962B2

Reaction notes

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