Tert-Butyl nitrite → 1-Azido-2-chloro-4-cyclopropylbenzene

HRID 1478798Notes

Reaction equation

HRID 1478798 reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([CH:9]2[CH2:11][CH2:10]2)[CH:6]=[CH:5][C:3]=1[NH2:4].N(OC(C)(C)C)=O.[Si]([N:23]=[N+:24]=[N-])(C)(C)C.C([O-])(O)=O.[Na+]>O>[N:4]([C:3]1[CH:5]=[CH:6][C:7]([CH:9]2[CH2:11][CH2:10]2)=[CH:8][C:2]=1[Cl:1])=[N+:23]=[N-:24]

Participants

6

Reactant 4

HCID 10906Tert-Butyl nitriteHCID 78378AzidotrimethylsilaneHCID 516892Sodium BicarbonateHCID 137730032-Chloro-4-cyclopropylaniline

Product 1

HCID 1185132641-Azido-2-chloro-4-cyclopropylbenzene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

2-Chloro-4-cyclopropylaniline (70 g, 418 mmol) was dissolved in Me-THF (2090 mL) and cooled to 0° C. in an ice bath. t-Butyl nitrite (59.8 mL, 501 mmol) was added slowly and TMSN3 (66.5 mL, 501 mmol) dropwise. The mixture was stirred at 0° C. for 30 min and gradually allowed to warm up to RT and stirred for 2 hrs. To the resulting mixture was added sat. NaHCO3 (aq) (250 mL) slowly under cooling, followed by water (250 mL). The mixture was transferred to a separating funnel and washed with water (1.5 L), dried over Na2SO4 and filtered to give the title compound which was used in the next step without further purification; HPLC Method D: Rt 5.63 mins;

Workup

  1. temperatureto warm up to RT
  2. stirringstirred for 2 hrs
  3. temperatureunder cooling
  4. customThe mixture was transferred to a separating funnel
  5. washwashed with water (1.5 L)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered

Sources & evidence

ORD record
ord-cc01f12260d8409e8d01ad89f9b5fddd
Source dataset
uspto-grants-2016_08
Patent number
US09403833B2

Reaction notes

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