Tetrahydrofuran → HCID 178418645, compound

HRID 5234Notes

Reaction equation

HRID 5234 reaction equation
Cl.[NH2:2][OH:3].C(N(CC)CC)C.[C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]1[CH:24]=[CH:23][C:22]([CH2:25][N:26]2[C:30]3[C:31]([C:35]([O:37][CH3:38])=[S:36])=[CH:32][CH:33]=[CH:34][C:29]=3[N:28]=[C:27]2[CH2:39][CH2:40][CH3:41])=[CH:21][CH:20]=1)#[N:12].O1CCCC1>CS(C)=O>[OH:3][NH:2][C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]1[CH:24]=[CH:23][C:22]([CH2:25][N:26]2[C:30]3[C:31]([C:35]([O:37][CH3:38])=[S:36])=[CH:32][CH:33]=[CH:34][C:29]=3[N:28]=[C:27]2[CH2:39][CH2:40][CH3:41])=[CH:21][CH:20]=1)=[NH:12]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 86747196Methyl 1-[(2'-cyanobiphenyl-4-yl)methyl]2-propylthiobenzimidazole-7-carboxylate

Product 1

HCID 178418645HCID 178418645, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of hydroxylamine hydrochloride (20.85 g) in DMSO (200 ml) was added triethylamine (3.9 g) and the mixture was stirred for 30 minutes at room temperatures. To the reaction mixture was added the compound (16 g) obtained in Example (34c), and the mixture was stirred for 60 hours at 70° C. To the resultant mixture was added tetrahydrofuran (100 ml). After removal of crystalline precipitate by filtration, the filtrate was concentrated to dryness. The residue was partitioned between water (1.2 liter) and ethyl acetate (350 ml), and the upper layer was washed with water (70 ml×3). Ethyl acetate was evaporated under reduced pressure, and to the residue was added methanol (70 ml). Resulting crystalline precipitate was filtered off. The filtrate was concentrated to dryness under reduced pressure to give the title compound as a pale yellow syrup (13.0 g, 76%).

Workup

  1. stirringthe mixture was stirred for 60 hours at 70° C
  2. customAfter removal of crystalline precipitate
  3. filtrationby filtration
  4. concentrationthe filtrate was concentrated to dryness
  5. customThe residue was partitioned between water (1.2 liter) and ethyl acetate (350 ml)
  6. washthe upper layer was washed with water (70 ml×3)
  7. customEthyl acetate was evaporated under reduced pressure
  8. additionto the residue was added methanol (70 ml)
  9. filtrationResulting crystalline precipitate was filtered off
  10. concentrationThe filtrate was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-d43f11dc297541b8b35b7cb26b75eb7f
Source dataset
uspto-grants-1993_09
Patent number
US05243054

Reaction notes

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