Sodium Hydroxide → 1-Azido-4-chloro-2-cyclopropylbenzene

HRID 1478804Notes

Reaction equation

HRID 1478804 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([CH:9]2[CH2:11][CH2:10]2)[CH:3]=1.N([O-])=O.[Na+].[N-:16]=[N+:17]=[N-].[Na+].[OH-].[Na+]>C(O)(=O)C.O>[N:6]([C:5]1[CH:7]=[CH:8][C:2]([Cl:1])=[CH:3][C:4]=1[CH:9]1[CH2:11][CH2:10]1)=[N+:16]=[N-:17]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 33557Sodium AzideHCID 183682604-Chloro-2-cyclopropylanilineHCID 23668193Sodium Nitrite

Product 1

HCID 1185132901-Azido-4-chloro-2-cyclopropylbenzene

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent3×

Conditions

Temperature
0 °C

Procedure

A solution of 4-chloro-2-cyclopropylaniline (182 mg, 1.086 mmol) in acetic acid (15 ml) and water (15 ml) was stirred and cooled to 0° C. A solution of sodium nitrite (74.9 mg, 1.086 mmol) in water (1.4 ml) was added dropwise and the mixture was stirred under ice cooling for 10 mins. A solution of sodium azide (70.6 mg, 1.086 mmol) in water (1.5 ml) was added dropwise and was stirred under ice cooling for 1 hr and then at RT 30 mins. To the product mixture was added 2M NaOH (aq) until basic and this was extracted with EtOAc. The organic extract was washed with sat. NaHCO3(aq) and dried over MgSO4, filtered and concentrated under reduced pressure to give the title compound as a dark yellow/brown oil. The crude product was used in the next step without further purification.

Workup

  1. stirringwas stirred under ice cooling for 1 hr
  2. customat RT
  3. custom30 mins
  4. extractionthis was extracted with EtOAc
  5. extractionThe organic extract
  6. washwas washed with sat. NaHCO3(aq)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f25f692a8c66490cb608476cbec56413
Source dataset
uspto-grants-2016_08
Patent number
US09403833B2

Reaction notes

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