Tetrahydrofuran → HCID 178507486, compound

HRID 1638321Notes

Reaction equation

HRID 1638321 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[S:11][CH:12]=[C:13]([C:15]([NH:17][C:18]2[NH:22][N:21]=[N:20][N:19]=2)=[O:16])[N:14]=1)([O-])=O.O1CCCC1>[Pd].CN(C=O)C>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[S:11][CH:12]=[C:13]([C:15]([NH:17][C:18]2[NH:22][N:21]=[N:20][N:19]=2)=[O:16])[N:14]=1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 178522726HCID 178522726, compound

Product 1

HCID 178507486HCID 178507486, compoundYield 89.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(2-nitrophenyl)-N-(1H-tetrazole-5-yl)-4-thiazolecarboxamide (200 mg) in a mixed solvent of dry tetrahydrofuran (THF, 30 ml) and dry DMF (13.7 ml) was added (10%) palladium on charcoal (200 mg) and the mixture was hydrogeneted for 22 hours. The catalyst was sucked off and the filtrate was concentrated under reduced pressure. The residue was treated with water (200 mg) to form crystals, which were filtered and dried to give colorless solids of 2-(2-aminophenyl)-N-(1H-tetrazole-5-yl)-4-thiazolecarboxamide (162 mg, 89%).

Workup

  1. concentrationthe filtrate was concentrated under reduced pressure
  2. additionThe residue was treated with water (200 mg)
  3. customto form crystals, which
  4. filtrationwere filtered
  5. customdried

Sources & evidence

ORD record
ord-a499aa2c3dde47ac911a9ad7d57b5963
Source dataset
uspto-grants-1989_11
Patent number
US04879295

Reaction notes

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