Methanol → HCID 69332815, compound

HRID 970434Notes

Reaction equation

HRID 970434 reaction equation
[CH3:1][N:2]([CH:4]=[N:5][S:6]([C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=1[O:18]C)(=[O:8])=[O:7])[CH3:3].B(Br)(Br)Br.CO.C(OC(C)C)(C)C>C(Cl)Cl>[CH3:3][N:2]([CH:4]=[N:5][S:6]([C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=1[OH:18])(=[O:7])=[O:8])[CH3:1]

Participants

6

Reactant 4

HCID 887MethanolHCID 7914Diisopropyl EtherHCID 25134Boron tribromide2×HCID 69332889HCID 69332889, compound

Product 1

HCID 69332815HCID 69332815, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of 2.82 g (9.8 mmol) of N-dimethylaminomethylene-2-methoxy-4-nitro-benzenesulfonamide in 70 ml of DCM is mixed slowly at room temperature with 13 ml of a 1 molar solution of boron tribromide in DCM. After 5 hours, 3 ml of the 1 molar solution of boron tribromide in DCM is added again, and it is stirred for another 16 hours. The batch is mixed with MeOH and diisopropyl ether. The precipitate that is formed is suctioned off, washed with EtOH and diisopropyl ether and dried. 1.94 g (7.1 mmol, corresponding to 72% of theory) of the product is obtained.

Workup

  1. customThe precipitate that is formed
  2. washwashed with EtOH and diisopropyl ether
  3. customdried
  4. custom1.94 g (7.1 mmol, corresponding to 72% of theory) of the product is obtained

Sources & evidence

ORD record
ord-178483c1066a4df096d125e53e6925c8
Source dataset
uspto-grants-2007_12
Patent number
US07312225B2

Reaction notes

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