Hydrochloric Acid → 2-Methyl-8-(phenylsulfonyl)-1,3,4,8-tetrahydro-2H-[1,4]oxazepino[6,7-e]indole

HRID 2423120Notes

Reaction equation

HRID 2423120 reaction equation
[CH3:1][N:2]1[CH2:15][C:7]2=[C:8]3[C:12](=[CH:13][CH:14]=[C:6]2[O:5][CH2:4][CH2:3]1)[NH:11][CH:10]=[CH:9]3.[H-].[Na+].[C:18]1([S:24](Cl)(=[O:26])=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.Cl>C([O-])([O-])=O.[Na+].[Na+].C(OCC)C.CN(C=O)C>[CH3:1][N:2]1[CH2:15][C:7]2=[C:8]3[C:12](=[CH:13][CH:14]=[C:6]2[O:5][CH2:4][CH2:3]1)[N:11]([S:24]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=[O:26])=[O:25])[CH:10]=[CH:9]3

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 672416342-Methyl-1,3,4,8-tetrahydro-2H-[1,4]oxazepino[6,7-e]indole2×

Product 1

HCID 250557762-Methyl-8-(phenylsulfonyl)-1,3,4,8-tetrahydro-2H-[1,4]oxazepino[6,7-e]indoleYield 47.6%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 10340Sodium CarbonateSolvent

Procedure

DMF (15 mL) was added to a vial containing 2-methyl-1,3,4,8-tetrahydro-2H-[1,4]oxazepino[6,7-e]indole (Intermediate 6, 0.250 g, 1.24 mmol) and sodium hydride (60% in mineral oil, 0.100 g, 2.50 mmol). The mixture was stirred for 20 minutes at room temperature before benzenesulfonyl chloride (0.327 g, 1.85 mmol) was added. The reaction was allowed to stir for 30 minutes before 2 M HCl (0.5 mL) was added and the mixture was diluted with 1 M Na2CO3 and diethylether. The organic phase was washed with water, dried (MgSO4) and evaporated. The crude product was dissolved in DCM (2 mL) and hexane (20 mL) was added. The mixture was allowed to stand overnight and the light yellow crystals were filtered and washed with hexane to give title compound (202 mg) as a light yellow solid. MS m/z 343 [M+H]+.

Workup

  1. additionwas added
  2. additionwas added
  3. washThe organic phase was washed with water
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. dissolutionThe crude product was dissolved in DCM (2 mL)
  7. additionhexane (20 mL) was added
  8. filtrationthe light yellow crystals were filtered
  9. washwashed with hexane

Sources & evidence

ORD record
ord-30a08a022a2f49e9bf54df47350ec1b8
Source dataset
uspto-grants-2011_06
Patent number
US07960374B2

Reaction notes

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