Tetrahydrofuran → HCID 22041814, compound

HRID 1791082Notes

Reaction equation

HRID 1791082 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([S:12]([NH:15][C:16]3[CH:17]=[CH:18][C:19]([Cl:26])=[C:20]([CH:25]=3)[C:21]([O:23][CH3:24])=[O:22])(=[O:14])=[O:13])=[CH:9]2)=[CH:4][CH:3]=1.[C:27](N1C=CN=C1)(N1C=CN=C1)=[S:28].C1COCC1>C(OCC)(=O)C>[Cl:26][C:19]1[CH:18]=[CH:17][C:16]([NH:15][S:12]([C:8]2[CH:7]=[CH:6][C:5]3[C:10](=[CH:11][C:2]([N:1]=[C:27]=[S:28])=[CH:3][CH:4]=3)[CH:9]=2)(=[O:14])=[O:13])=[CH:25][C:20]=1[C:21]([O:23][CH3:24])=[O:22]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 802641,1'-ThiocarbonyldiimidazoleHCID 22041793HCID 22041793, compound

Product 1

HCID 22041814HCID 22041814, compoundYield 95.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 4.5 g (11.5 mmol) of compound 134 and 9.01 g (50.6 mmol) of 1,1′-thiocarbonyldiimidazole was added 50 mL of THF. The solution was allowed to stir at ambient temperature for 1.5 hours. Then, the reaction was poured into 300 mL of ethyl acetate and extracted with 1N HCl, water, and brine. The organic layer was dried (MgSO4), filtered, and the volatiles removed by rotary evaporation to yield 4.77 g of compound 135.

Workup

  1. extractionextracted with 1N HCl, water, and brine
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. customthe volatiles removed by rotary evaporation

Sources & evidence

ORD record
ord-c2b8f19994364a4d98d0897d016a3821
Source dataset
uspto-grants-2006_07
Patent number
US07071231B2

Reaction notes

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