Water → HCID 53417180, compound

HRID 1844701Notes

Reaction equation

HRID 1844701 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Br:11])[CH:10]=1)[C:5](O)=[O:6].Cl.[CH3:13][NH:14][O:15][CH3:16].C(N=[N+]=[N-])C.O>O=S(Cl)Cl.C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Br:11])[CH:10]=1)[C:5]([N:14]([O:15][CH3:16])[CH3:13])=[O:6]

Participants

7

Reactant 4

HCID 962WaterHCID 12063Benzoic acid, 3,5-dibromo-HCID 79118Ethane, azido-HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)

Product 1

HCID 53417180HCID 53417180, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 24386Thionyl ChlorideSolvent

Procedure

The solution of 3,5-dibromobenzoic acid (26 g, 93 mmol) in SOCl2 (100 mL) was heated at reflux for 2 h, concentrated, diluted with dry DCM (300 mL) and added slowly to a stirred solution of N,O-dimethylhydroxylamine hydrochloride (9.75 g, 100 mmol) and EtN3 (28 g, 277 mmol) in dry DCM (300 mL) at 0° C. The solution was stirred for 1 h at rt, poured into water and the organic layer was separated. The organic layer was washed with water and brine, dried over Na2SO4, filtered and concentrated to give crude compound P37a (28 g, 93%) as an oil.

Workup

  1. temperatureat reflux for 2 h
  2. concentrationconcentrated
  3. additiondiluted with dry DCM (300 mL)
  4. customthe organic layer was separated
  5. washThe organic layer was washed with water and brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give crude compound P37a (28 g, 93%) as an oil

Sources & evidence

ORD record
ord-a71840bae54548e9944a5090f50bb903
Source dataset
uspto-grants-2015_02
Patent number
US08946446B2

Reaction notes

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