Acetic Acid → HCID 178465650, compound

HRID 2291590Notes

Reaction equation

HRID 2291590 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8](=[O:10])[N:7]([CH2:11][C:12]([N:14]3[CH2:19][CH2:18][N:17]([NH:20][C:21](=[NH:36])[CH2:22]C(OCC4C=CC([N+]([O-])=O)=CC=4)=O)[CH2:16][CH2:15]3)=[O:13])[C:6]=2[CH:37]=1.C(O)(=O)C.O>[Pd].O1CCCC1.CO>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8](=[O:10])[N:7]([CH2:11][C:12]([N:14]3[CH2:19][CH2:18][N:17]([NH:20][C:21](=[NH:36])[CH3:22])[CH2:16][CH2:15]3)=[O:13])[C:6]=2[CH:37]=1

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 178511206HCID 178511206, compound

Product 1

HCID 178465650HCID 178465650, compoundYield 40.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5-chloro-3-{[4-[N-(p-nitrobenzyloxycarbonyl)acetimidoylamino]-1-piperazinyl]carbonylmethyl}-2-benzothiazolinone (2.0 g), acetic acid (0.3 ml), water (3 ml), 10% palladium on carbon (2.0 g) in tetrahydrofuran (40 ml) and methanol (20 ml) was incubated under an atmosphere of hydrogen for 3 hours. Palladium on carbon was filtered off, and the filtrate was coevaporated with ethanol. The residue obtained was purified by aluminum column chromatography, treated with hydrogen chloride in ethanol, and recrystallized from a mixture of water, ethanol and ether to give yellow crystals of 5-chloro-3-[(4-acetimidoylamino-1-piperazinyl)carbonylmethyl]-2-benzothiazolinone hydrochloride (0.3 g).

Workup

  1. filtrationPalladium on carbon was filtered off
  2. customThe residue obtained
  3. customwas purified by aluminum column chromatography
  4. additiontreated with hydrogen chloride in ethanol
  5. customrecrystallized from a mixture of water, ethanol and ether

Sources & evidence

ORD record
ord-282ed1c773e14086aa001a16e29ea169
Source dataset
uspto-grants-1989_01
Patent number
US04797399

Reaction notes

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