Hexane → N,N,5-Trimethyl-4-[(2,3,4,9-tetrahydro-9-methyl-4-oxo-1H-carbazol-3-yl) methyl]-1H-imidazole-1-sulphonamide

HRID 1723289Notes

Reaction equation

HRID 1723289 reaction equation
[CH3:1][N:2]([CH3:7])[S:3](Cl)(=[O:5])=[O:4].[CH3:8][N:9]1[C:21]2[CH2:20][CH2:19][CH:18]([CH2:22][C:23]3[N:24]=[CH:25][NH:26][C:27]=3[CH3:28])[C:17](=[O:29])[C:16]=2[C:15]2[C:10]1=[CH:11][CH:12]=[CH:13][CH:14]=2.C(N(CC)CC)C.CCCCCC>ClCCl>[CH3:1][N:2]([CH3:7])[S:3]([N:26]1[C:27]([CH3:28])=[C:23]([CH2:22][CH:18]2[C:17](=[O:29])[C:16]3[C:15]4[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=4)[N:9]([CH3:8])[C:21]=3[CH2:20][CH2:19]2)[N:24]=[CH:25]1)(=[O:5])=[O:4]

Participants

6

Reactant 4

HCID 8058HexaneHCID 8471TriethylamineHCID 83372Dimethylsulphamoyl chlorideHCID 172316GR 67330

Product 1

HCID 14233929N,N,5-Trimethyl-4-[(2,3,4,9-tetrahydro-9-methyl-4-oxo-1H-carbazol-3-yl) methyl]-1H-imidazole-1-sulphonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of dimethylsulphamoyl chloride (0.16 ml) in dry dichloromethane was added to a stirred solution of 1,2,3,9tetrahydro-9-methyl-3[(5-methyl-1H-imidazol-4-yl)methyl]-4H-carbazol-4-one (438 mg) and triethylamine (0.25 ml) in dry dichloromethane (30 ml) and the mixture was heated at reflux for 18 h. After cooling the reaction mixture was adsorbed onto FCC silica which was then applied to a column and FCC eluting with System A (150:8:1) gave an oil, which solidified to a powder on trituration with dry hexane (30 ml). This powder was then further purified by dissolution in dry dichloromethane (30 ml) and crystallisation by addition of dry hexane (10 ml) to give the title compound (518 mg), m.p. 122°-124°.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 18 h
  3. temperatureAfter cooling the reaction mixture
  4. washeluting with System A (150:8:1)
  5. customgave an oil, which
  6. customThis powder was then further purified by dissolution in dry dichloromethane (30 ml)
  7. customcrystallisation
  8. additionby addition of dry hexane (10 ml)

Sources & evidence

ORD record
ord-99cf2beceda742bf8f701e9a37d2a4da
Source dataset
uspto-grants-1989_08
Patent number
US04859662

Reaction notes

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