Hydrochloric Acid → HCID 21278850, compound

HRID 2291583Notes

Reaction equation

HRID 2291583 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]([N:20]=O)[CH2:16][CH2:15]3)=[O:13])[C:6]=2[CH:22]=1.C(Cl)(Cl)Cl.CO.Cl>O.C(O)(=O)C.CCOCC.[Zn]>[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[CH2:15][CH2:16][N:17]([NH2:20])[CH2:18][CH2:19]3)=[O:13])[C:6]=2[CH:22]=1

Participants

9

Reactant 4

HCID 313Hydrochloric Acid2×HCID 887MethanolHCID 6212ChloroformHCID 21278875HCID 21278875, compound

Product 1

HCID 21278850HCID 21278850, compoundYield 82.2%

Reagents, catalysts & solvents 4

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

5-Chloro-3-[(4-nitroso-1-piperazinyl)carbonylmethyl]-2-benzothiazolinone (9.2 g) was dissolved in a mixture of water (120 ml) and acetic acid (400 ml). To the solution stirred at room temperature zinc dust (12.0 g) was added over 3 hours. The mixture was stirred for additional 2 hours at room temperature. The zinc dust unused in the reaction was filtered and washed once with acetic acid. The filtrate and the washing were combined and evaporated to dryness. Chloroform (200 ml) was added to the residue and insoluble material was then filtered. The chloroform solution was concentrated to give a syrup which was subjected to a silica gel column chromatography using a mixture of chloroform and methanol (10:1). The desired fractions were combined and evaporated to give a pale yellow oil which was converted into hydrochloride using hydrogen chloride in absolute ether. The crude crystals obtained were recrystallized from aqueous ethanol to give 5-chloro-3-[(4-amino-1-piperazinyl)carbonylmethyl]-2-benzothiazolinone hydrochloride (4.03 g).

Workup

  1. additionwas added over 3 hours
  2. filtrationThe zinc dust unused in the reaction was filtered
  3. washwashed once with acetic acid
  4. customevaporated to dryness
  5. additionChloroform (200 ml) was added to the residue and insoluble material
  6. filtrationwas then filtered
  7. concentrationThe chloroform solution was concentrated
  8. customto give a syrup which
  9. customevaporated
  10. customto give a pale yellow oil which
  11. customThe crude crystals obtained
  12. customwere recrystallized from aqueous ethanol

Sources & evidence

ORD record
ord-23cd495c28fc423092d83119ef81e7f4
Source dataset
uspto-grants-1989_01
Patent number
US04797399

Reaction notes

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