Thionyl Chloride → HCID 67131071, compound

HRID 1678648Notes

Reaction equation

HRID 1678648 reaction equation
[N:1]([C:4]1[CH:19]=[C:18]([F:20])[C:17]([F:21])=[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-].S(Cl)([Cl:24])=O>>[Cl:24][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]=[C:17]([F:21])[C:18]([F:20])=[CH:19]2

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 86640285HCID 86640285, compound

Product 1

HCID 67131071HCID 67131071, compoundYield 94%

Procedure

2-Azido-N-(4-chloro-phenyl)-4,5-difluoro-benzamide (18.5 g, 60 mmol) was suspended in thionyl chloride (193 ml). The suspension was heated under reflux conditions for 14 h. The solvent was removed under reduced pressure. The residue was dissolved in dichloromethane. Under ice cooling saturated NaHCO3 solution was added until pH 8 was reached. The mixture was extracted two times with dichloromethane, the combined extracts were washed with ice water/brine 1/1 and dried over Na2SO4. The solvent was removed under reduced pressure to give a brown solid which was crystallized from methanol/dichloromethane/n-heptane to give the title compound (16.8 g, 56 mmol; 94%) as off-white crystals. MS: m/e=299.5 [M+H+].

Workup

  1. temperatureThe suspension was heated under reflux conditions for 14 h
  2. customThe solvent was removed under reduced pressure
  3. dissolutionThe residue was dissolved in dichloromethane
  4. additionUnder ice cooling saturated NaHCO3 solution was added until pH 8
  5. extractionThe mixture was extracted two times with dichloromethane
  6. washthe combined extracts were washed with ice water/brine 1/1
  7. dry with materialdried over Na2SO4
  8. customThe solvent was removed under reduced pressure
  9. customto give a brown solid which
  10. customwas crystallized from methanol/dichloromethane/n-heptane

Sources & evidence

ORD record
ord-a420dfd96bf846e6b4f9f8f9f75f38ef
Source dataset
uspto-grants-2011_08
Patent number
US08008505B2

Reaction notes

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