Sodium hydride → 2-Nitro 6,7,8,9-tetrahydro-5-thia-8-aza-benzocycloheptene

HRID 1687241Notes

Reaction equation

HRID 1687241 reaction equation
[H-].[Na+].Cl.Cl[C:5]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:6]=1[CH2:7][NH:8][CH2:9][CH2:10][SH:11]>CN(C=O)C>[N+:16]([C:13]1[CH:14]=[CH:15][C:5]2[S:11][CH2:10][CH2:9][NH:8][CH2:7][C:6]=2[CH:12]=1)([O-:18])=[O:17]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 866338952-(2-Chloro-5-nitro-benzylamino)-ethanethiol hydrochloride

Product 1

HCID 578538112-Nitro 6,7,8,9-tetrahydro-5-thia-8-aza-benzocyclohepteneYield 49.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a slurry of sodium hydride (1.06 g, 0.01 mol) in anhydrous DMF (175 mL) under nitrogen was added 2-(2-chloro-5-nitro-benzylamino)-ethanethiol hydrochloride (3.0 g, 0.01 mol), stirred 3 hrs. and evaporated. The residue was treated with water (15 mL) giving 2-nitro 6,7,8,9-tetrahydro-5-thia-8-aza-benzocycloheptene (1.05 g, 47%) as a tan solid. MP: 104-5° C.; 1H-NMR (DMSO-d6) δ 8.13 (s, 1H), 7.97-8.00 (d, 1H), 7.69-7.10 (s, 1H), 4.04 (s, 2H), 3.12-20 (d, 2H), 2.82-8 (d, 2H), 2.54-65 (br, 1H); LC/MS (ESI+): 210 (M).

Workup

  1. customand evaporated
  2. additionThe residue was treated with water (15 mL)

Sources & evidence

ORD record
ord-543805d4081745bb9816a92d25e5dfea
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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