HCID 15729139, compound → HCID 15729140, compound

HRID 2380581Notes

Reaction equation

HRID 2380581 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-513f1b1162294820b378b14d0014f140
Source dataset
uspto-grants-1994_11
Patent number
US05369107

Reaction notes

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