Acetic Acid → HCID 15729143, compound

HRID 2380583Notes

Reaction equation

HRID 2380583 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[O:17])[C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][CH:9]=2)[N:6]=1.CO.C(O)(=O)C>[Pd].O1CCCC1>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[O:17])[C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=2)[N:6]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 887MethanolHCID 15729142HCID 15729142, compound

Product 1

HCID 15729143HCID 15729143, compoundYield 87.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-amino-4-(4-nitrobenzoyl)thiazole g) and 10% palladium on carbon (1 g, 50% wet) in a mixture of tetrahydrofuran (50 ml), methanol (50 ml) and acetic acid (5 ml) was hydrogenated under atmospheric pressure for 7 hours. The reaction mixture was filtered and then, the filtrate was concentrated under reduced pressure. The residue was dissolved in water and adjusted to pH using aqueous sodium bicarbonate. The precipitates were collected by filtration, washed with water and dried in vacuo to give 2-amino-4(4-aminobenzoyl)thiazole (0.54 g, yield: 87.7%).

Workup

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

Sources & evidence

ORD record
ord-5cc66fc7a30146b99b082cd5220e04a9
Source dataset
uspto-grants-1994_11
Patent number
US05369107

Reaction notes

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