Water → HCID 68602742, compound

HRID 641352Notes

Reaction equation

HRID 641352 reaction equation
[CH3:1][N:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[C:5]([CH3:12])=[CH:4][S:3]1(=[O:14])=[O:13].[Br:15]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N.O>ClCCCl.C(Cl)Cl>[Br:15][C:4]1[S:3](=[O:13])(=[O:14])[N:2]([CH3:1])[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[C:5]=1[CH3:12]

Participants

7

Reactant 4

HCID 962WaterHCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 21816153HCID 21816153, compound

Product 1

HCID 68602742HCID 68602742, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

390 mg of 1,4-dimethyl-1H-benzo[c][1,2]thiazin-2,2-dioxide in 20 ml 1,2-dichloroethane are combined with 332 mg of N-bromosuccinimide and 50 mg of 2,2′-azodiisobutyronitrile. The yellow solution is refluxed for a total of 10 h and then left to stand for another two days at ambient temperature. The reaction mixture is distributed between water and methylene chloride, the organic phase is washed with water, dried over magnesium sulphate and evaporated down. A yellowish resin is left which is purified through a silica gel column with petroleum ether/ethyl acetate (5:1 to 4:1) as eluant. A mixture of 4-bromo-methyl-1-methyl-1H-benzo[c][1,2]thiazin-2,2-dioxide and 3-bromo-1,4-dimethyl-1H-benzo[c][1,2]thiazin-2,2-dioxide is obtained, which is further reacted as it is.

Workup

  1. temperatureThe yellow solution is refluxed for a total of 10 h
  2. waitleft
  3. washthe organic phase is washed with water
  4. dry with materialdried over magnesium sulphate
  5. customevaporated down
  6. waitA yellowish resin is left which
  7. customis purified through a silica gel column with petroleum ether/ethyl acetate (5:1 to 4:1) as eluant
  8. additionA mixture of 4-bromo-methyl-1-methyl-1H-benzo[c][1,2]thiazin-2,2-dioxide

Sources & evidence

ORD record
ord-3e3ce9ab8c8040d1bb01e7e9f41b1c67
Source dataset
uspto-grants-2010_04
Patent number
US07696212B2

Reaction notes

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