Water → HCID 21278901, compound

HRID 2291586Notes

Reaction equation

HRID 2291586 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[O:10])=[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.C(N(CC)CC)C.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:9]([NH:8][C:5]4[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=4)=[O:10])[CH2:29][CH2:30]3)=[O:24])[C:17]=2[CH:32]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 709554-Fluorophenyl isocyanateHCID 21278850HCID 21278850, compound

Product 1

HCID 21278901HCID 21278901, compoundYield 88.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 4-fluorophenyl isocyanate (273 mg) in dioxane (5 ml) was added dropwise to a mixture of 5-chloro-3-[(4-amino-1-piperazinyl)carbonylmethyl]-2-benzothiazolinone hydrochloride (981 mg), triethylamine (273 mg), dioxane (40 ml) and water (2 ml) at room temperature. The resulting mixture was stirred for 2 hours and concentrated under reduced pressure. The residue was filtered, washed with water and ethyl acetate, and recrystallized from N,N-dimethylformamide to give 5-chloro-3-{[4-[N'-(4-fluorophenyl)ureido]-1-piperazinyl]carbonylmethyl}-2-benzothiazolinone (0.82 g).

Workup

  1. concentrationconcentrated under reduced pressure
  2. filtrationThe residue was filtered
  3. washwashed with water and ethyl acetate
  4. customrecrystallized from N,N-dimethylformamide

Sources & evidence

ORD record
ord-e26784297d794262bb6464a2dd1b5d2e
Source dataset
uspto-grants-1989_01
Patent number
US04797399

Reaction notes

Loading…