HCID 15729139, compound → HCID 15729140, compound

HRID 1656935Notes

Reaction equation

HRID 1656935 reaction equation
[NH2:1][C:2]1[S:3][C:4]([C:10](=[O:20])[C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=2)=[C:5]([C:7]([OH:9])=[O:8])[N:6]=1>[Pd].CO.O1CCCC1>[NH2:1][C:2]1[S:3][C:4]([C:10](=[O:20])[C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=2)=[C:5]([C:7]([OH:9])=[O:8])[N:6]=1

Participants

5

Reactant 1

HCID 15729139HCID 15729139, compound

Product 1

HCID 15729140HCID 15729140, compoundYield 90%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-amino-5-(4-nitrobenzoyl)-4-thiazolecarboxylic acid (2.6 g) and 10% palladium on carbon (1 g, 50% wet) in a mixture of methanol (50 ml) and tetrahydrofuran (50 ml) was hydrogenated under atmospheric pressure for 2 hours. The reaction mixture was filtered and then the filtrate was concentrated under reduced pressure. The residue was triturated with ether and the precipitates were collected by filtration, washed with ether and dried in vacuo to give 2-amino-5-(4-aminobenzoyl)-4-thiazolecarboxylic acid (2.10 g, yield: 90.0%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was triturated with ether
  4. filtrationthe precipitates were collected by filtration
  5. washwashed with ether
  6. customdried in vacuo

Sources & evidence

ORD record
ord-9cf5499ae80c4d60b98c8057cd00e74d
Source dataset
uspto-grants-1993_10
Patent number
US05256675

Reaction notes

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