Tert-Butyl nitrite → HCID 90303242, compound

HRID 1051922Notes

Reaction equation

HRID 1051922 reaction equation
N[C:2]1[S:3][C:4]2[CH:9]([C:10]#[N:11])[CH2:8][CH2:7][C:5]=2[N:6]=1.N(OC(C)(C)C)=O>C1COCC1>[S:3]1[C:4]2[CH:9]([C:10]#[N:11])[CH2:8][CH2:7][C:5]=2[N:6]=[CH:2]1

Participants

4

Reactant 2

HCID 10906Tert-Butyl nitriteHCID 90303417HCID 90303417, compound

Product 1

HCID 90303242HCID 90303242, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

To a soln. of 2-amino-5,6-dihydro-4H-cyclopenta[d]thiazole-6-carbonitrile (1.00 g, 6.05 mmol) in THF (54 mL) was added tert-butyl nitrite (1.04 g, 9.08 mmol) and the mixture was stirred at 65° C. for 3 h. Subsequently, the mixture was quenched with aq. sat. NaHCO3 and extracted with EtOAc. The comb. org. layers were washed with brine, dried over MgSO4, and conc. in vacuo. Purification by means of CC (10-80% EtOAc/Hept) provided a yellow oil.

Workup

  1. customSubsequently, the mixture was quenched with aq. sat. NaHCO3
  2. extractionextracted with EtOAc
  3. washlayers were washed with brine
  4. dry with materialdried over MgSO4
  5. customPurification by means of CC (10-80% EtOAc/Hept)
  6. customprovided a yellow oil

Sources & evidence

ORD record
ord-f3a2dc1760a343b893d9150e8f4b7b90
Source dataset
uspto-grants-2016_07
Patent number
US09388197B2

Reaction notes

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