Benzo(d)thiazol-2-amine → HCID 9932706, compound

HRID 429863Notes

Reaction equation

HRID 429863 reaction equation
[CH2:1]([CH:3]([CH2:19][CH3:20])[CH:4]([N:14]1[CH:18]=[CH:17][N:16]=[CH:15]1)[C:5]1[CH:10]=[CH:9][C:8]([N:11]=[C:12]=[S:13])=[CH:7][CH:6]=1)[CH3:2].[S:21]1[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[N:23]=[C:22]1[NH2:30]>C(#N)C>[S:21]1[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[N:23]=[C:22]1[NH:30][C:12]([NH:11][C:8]1[CH:7]=[CH:6][C:5]([CH:4]([N:14]2[CH:18]=[CH:17][N:16]=[CH:15]2)[CH:3]([CH2:1][CH3:2])[CH2:19][CH3:20])=[CH:10][CH:9]=1)=[S:13]

Participants

4

Reactant 2

HCID 8706Benzo(d)thiazol-2-amineHCID 22335512HCID 22335512, compound

Product 1

HCID 9932706HCID 9932706, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-[2-ethyl-1-(4-isothiocyanatophenyl)butyl]-1H-imidazole (0.0123 mol) and 2-benzothiazolamine (0.0148 mol) in acetonitrile (80 ml) was stirred and refluxed for 12 hours. The solvent was evaporated and the residue was taken up in H2O and CH2Cl2. The organic layer was separated, dried, filtered and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 97.5/2.5/0.1). The desired fractions were collected and the solvent was evaporated. The residue was purified again by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 85/15/0.1). The pure fractions were collected and the solvent was evaporated. The residue was crystallized from 2-butanone and DIPE. The precipitate was filtered off and dried, yielding 0.44 g (9%) (±)-N-(2-benzothiazolyl)-N′-[4-[1-(1H-imidazol-1-yl)-2-ethylbutyl]phenyl]-thiourea (compound 705).

Workup

  1. temperaturerefluxed for 12 hours
  2. customThe solvent was evaporated
  3. customThe organic layer was separated
  4. customdried
  5. filtrationfiltered
  6. customthe solvent was evaporated
  7. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 97.5/2.5/0.1)
  8. customThe desired fractions were collected
  9. customthe solvent was evaporated
  10. customThe residue was purified again by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 85/15/0.1)
  11. customThe pure fractions were collected
  12. customthe solvent was evaporated
  13. customThe residue was crystallized from 2-butanone and DIPE
  14. filtrationThe precipitate was filtered off
  15. customdried

Sources & evidence

ORD record
ord-4d4477b8540a4cf290ef8ee22c106931
Source dataset
uspto-grants-2001_11
Patent number
US06319939B1

Reaction notes

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