Dichloromethane → HCID 66905406, compound

HRID 1690590Notes

Reaction equation

HRID 1690590 reaction equation
[N:1]([C:4]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:5]=1[C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1)=O)=[N+]=[N-].C(Cl)[Cl:22]>S(Cl)(Cl)=O>[Cl:22][C:6]1[N:8]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)[N:1]=[C:4]2[C:5]=1[CH:16]=[CH:17][C:18]([F:20])=[CH:19]2

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 86640271HCID 86640271, compound

Product 1

HCID 66905406HCID 66905406, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

2-Azido-N-(4-chloro-phenyl)-4-fluoro-benzamide (2.7 g, 1 mmol) was dissolved at ambient temperature in thionyl chloride (18.2 ml) under an argon atmosphere. The reaction mixture was heated under reflux conditions for 14 h and brought to dryness under reduced pressure. The residue was taken up in ice water/saturated aqueous NaHCO3 solution 1/1 and CH2Cl2. The layers were separated and the aqueous layer was extracted one more time with CH2Cl2. The combined extracts were washed with ice water/brine 1/1 and dried over Na2SO4. The solvent was removed under reduced pressure to give the title compound (2.47 g, 8.8 mmol; 95%) as yellow solid. MS: m/e=280.9 [M+H+].

Workup

  1. temperatureThe reaction mixture was heated under reflux conditions for 14 h
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted one more time with CH2Cl2
  4. washThe combined extracts were washed with ice water/brine 1/1
  5. dry with materialdried over Na2SO4
  6. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-2dfece86d2734c7bba6c808665f01bb3
Source dataset
uspto-grants-2012_04
Patent number
US08153663B2

Reaction notes

Loading…