Water → 2-Tert-butyl-6-nitro-5-[4-phenylpiperazin-1-yl]benzothiazole

HRID 2118750Notes

Reaction equation

HRID 2118750 reaction equation
[C:1]([C:5]1[S:6][C:7]2[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[C:11](Cl)=[CH:10][C:8]=2[N:9]=1)([CH3:4])([CH3:3])[CH3:2].O.[C:19]1([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>>[C:1]([C:5]1[S:6][C:7]2[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[C:11]([N:28]3[CH2:29][CH2:30][N:25]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH2:26][CH2:27]3)=[CH:10][C:8]=2[N:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 962WaterHCID 70961-PhenylpiperazineHCID 197942022-Tert-butyl-5-chloro-6-nitrobenzothiazole

Product 1

HCID 201929552-Tert-butyl-6-nitro-5-[4-phenylpiperazin-1-yl]benzothiazole

Procedure

A mixture of 7 g of 2-tert-butyl-5-chloro-6-nitrobenzothiazole described in Example 5, in 8.2 g of N-phenylpiperazine is heated at 150°-160° for 12 hours, cooled and poured into water. The paste is extracted with methylene chloride, washed with 2N HCl, then with 10% NaOH and then with water. The organic layer is dried, the solvent evaporated and the solid crystallised from isopropyl alcohol to give 2-tert-butyl-6-nitro-5-[4-phenylpiperazin-1-yl]benzothiazole, melting at 152°-155°.

Workup

  1. temperatureis heated at 150°-160° for 12 hours
  2. temperaturecooled
  3. extractionThe paste is extracted with methylene chloride
  4. washwashed with 2N HCl
  5. customThe organic layer is dried
  6. customthe solvent evaporated
  7. customthe solid crystallised from isopropyl alcohol

Sources & evidence

ORD record
ord-d21f091a14494fe698eebfb69a479ee2
Source dataset
uspto-grants-1987_07
Patent number
US04680301

Reaction notes

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