Isopropanol → HCID 53913873, compound

HRID 1708534Notes

Reaction equation

HRID 1708534 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH:8]=[CH:9][N:10]([CH3:12])[CH3:11])[C:5]([Cl:13])=[CH:4][C:3]=1[N+:14]([O-:16])=[O:15].[S:17]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[C:19]([N:26]2[CH2:31]CNC[CH2:27]2)=[N:18]1.C(O)(C)C>C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([CH:8]=[CH:9][N:10]2[CH2:12][CH2:27][N:26]([C:19]3[C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[S:17][N:18]=3)[CH2:31][CH2:11]2)[C:5]([Cl:13])=[CH:4][C:3]=1[N+:14]([O-:16])=[O:15]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 27721443-(1-Piperazinyl)-1,2-benzisothiazoleHCID 53750001HCID 53750001, compound

Product 1

HCID 53913873HCID 53913873, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2,5-Dichloro-4-(2-dimethylaminoethenyl)-nitrobenzene (15 g, 0.057 mol) and 4-(1,2-benzisothiazol-3-yl)-piperazine (18.9 g, 0.086 mol) were combined in acetic acid (150 ml) and stirred overnight at room temperature under a nitrogen atmosphere. The slurry was poured slowly into a mixture of hexanes (300 ml) and isopropanol (300 ml) with stirring. The product was isolated by filtration as a brick red solid and washed with hexanes. The yield was 23.4 g, 93%; mp 194°-5° C. NMR (CDCl3) δ 8.05 (s, 1), 7.95-7.80 (m, 2), 7.56-7.35 (m, 3), 7.01 (d, 1), 5.60 (d, 1), 3.95-3.46 (m, 8). Analysis Calculated for C19H16N4O2Cl2S: C, 52.41; H, 3.70; N, 12.87. Found: C, 52.05; H, 3.36; N, 12.58.

Workup

  1. stirringwith stirring
  2. customThe product was isolated by filtration as a brick red solid
  3. washwashed with hexanes

Sources & evidence

ORD record
ord-bb8b5bfb2e304da7abda7ed14f8976d1
Source dataset
uspto-grants-1994_10
Patent number
US05359068

Reaction notes

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