Hydrochloric Acid → HCID 5148325, compound

HRID 1182207Notes

Reaction equation

HRID 1182207 reaction equation
CC([O-])(C)C.[K+].[C:7]([NH2:13])(=[O:12])[CH2:8][C:9](C)=O.[C:14]1([N:20]=C=S)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.Cl.CC1C=CC([S:31]([N-:34][N+:35]#N)(=O)=O)=CC=1>C1COCC1.C(O)C.C(N(CC)CC)C.O>[C:14]1([NH:20][C:9]2[S:31][N:34]=[N:35][C:8]=2[C:7]([NH2:13])=[O:12])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

10

Reactant 5

HCID 313Hydrochloric AcidHCID 7673Phenyl IsothiocyanateHCID 80077Acetoacetamide2×HCID 23665647Potassium tert-butoxideHCID 178427626HCID 178427626, compound

Product 1

HCID 5148325HCID 5148325, compoundYield 64%

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8471TriethylamineSolvent

Conditions

Temperature
45 °C

Procedure

To an ice cooled THF solution of t-BuOK (1.0 mmol) in a flask was added acetoacetamide (0.10 g, 1.0 mmol) in anhydrous THF. Phenyl isothiocyanate solution (0.15 g, 1.1 mmol) was added slowly to the flask with stirring 15 minutes after the addition of acetoacetamide. The reaction mixture was stirred at room temperature for about 2 h. Then 2 mL of water was added to the reaction mixture and it was kept stirring at room temperature for about 1 h. The pH of the solution was adjusted with 2 N HCl solution to about 5. The organic layer was separated and the solvent was removed. The solid obtained was then dissolved in anhydrous ethanol. Triethylamine (0.1 mL) and p-tosyl azide (0.2 g, 1.0 mmol) were added to the solution sequentially. The mixture was warmed up to 45° C. and stirred for about 30 minutes. The solid precipitate from the reaction mixture was collected, washed with cold ethanol and dried. This process yielded 0.14 g (64%) of the desired product, characterized as follows: m.p.: 195-197° C. 1H NMR (ppm, in DMSO-d6): 11.01 (s, 1H), 8.36 (s, 1H), 7.88 (s, 1H), 7.15-7.60 (m, 5H). FTIR (cm−1, KBr pellet): 3367, 1680, 1648, 1595, 1551, 1470, 1449, 1313, 1251, 1080, 877, 793, 747, 650. Mass spectrum (E1): 220 (75%, M+), 192, (42%, (M-28)+), 77 (100%, C6H5+).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for about 2 h
  2. stirringwas kept stirring at room temperature for about 1 h
  3. customThe organic layer was separated
  4. customthe solvent was removed
  5. customThe solid obtained
  6. stirringstirred for about 30 minutes
  7. customThe solid precipitate from the reaction mixture was collected
  8. washwashed with cold ethanol
  9. customdried

Sources & evidence

ORD record
ord-453a5347c286430f8db660115531634f
Source dataset
uspto-grants-2007_10
Patent number
US07288556B2

Reaction notes

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