Water → HCID 21278855, compound

HRID 2291585Notes

Reaction equation

HRID 2291585 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.Cl.[Cl:12][C:13]1[CH:14]=[CH:15][C:16]2[S:20][C:19](=[O:21])[N:18]([CH2:22][C:23]([N:25]3[CH2:30][CH2:29][N:28]([NH2:31])[CH2:27][CH2:26]3)=[O:24])[C:17]=2[CH:32]=1.[OH-].[Na+].O>O1CCOCC1>[Cl:12][C:13]1[CH:14]=[CH:15][C:16]2[S:20][C:19](=[O:21])[N:18]([CH2:22][C:23]([N:25]3[CH2:26][CH2:27][N:28]([NH:31][C:6](=[O:7])[C:5]4[CH:9]=[CH:10][C:2]([F:1])=[CH:3][CH:4]=4)[CH2:29][CH2:30]3)=[O:24])[C:17]=2[CH:32]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 678794-Fluorobenzoyl chlorideHCID 21278850HCID 21278850, compound

Product 1

HCID 21278855HCID 21278855, compoundYield 56.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 4-fluorobenzoyl chloride (761 mg) in dioxane (3 ml) was added dropwise to a mixture of 5-chloro-3-[(4-amino-1-piperazinyl)carbonylmethyl]-2-benzothiazolinone hydrochloride (872 mg), 1N-NaOH (5.3 ml), dioxane (30 ml) and water (5 ml) at 5° C. The resulting mixture was stirred for 30 minutes and concentrated under reduced pressure. The residue obtained was filtered, washed with water and ethyl acetate, and recrystallized from methanol to give 5-chloro-3-{[4-(4-fluorobenzamido)-1-piperazinyl]carbonylmethyl}-2-benzothiazolinone (0.61 g).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue obtained
  3. filtrationwas filtered
  4. washwashed with water and ethyl acetate
  5. customrecrystallized from methanol

Sources & evidence

ORD record
ord-54eb258c65b8463785fe506af623b1e7
Source dataset
uspto-grants-1989_01
Patent number
US04797399

Reaction notes

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