Tert-Butyl nitrite → HCID 59542484, compound

HRID 1809090Notes

Reaction equation

HRID 1809090 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[S:8][C:7]=1N)=[O:5])[CH3:2].N(OC(C)(C)C)=O.[Cl-].[NH4+]>[Cu](Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[S:8][CH:7]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 10906Tert-Butyl nitriteHCID 25517Ammonium ChlorideHCID 59542544HCID 59542544, compound

Product 1

HCID 59542484HCID 59542484, compoundYield 76.7%

Reagents, catalysts & solvents 1

HCID 24014Cupric ChlorideCatalyst

Procedure

2-Amino-5-(cyclohexyl)-thiophene-3-carboxylic acid ethyl ester (1.79 g, 7 mmol) was added to a mixture of t-butyl nitrite (10.5 mmol) and copper (II) chloride (7 mmol) in IMS (100 mL). The reaction mixture was stirred for 30 minutes then saturated aqueous ammonium chloride (7 mL) was added and the resulting solution stirred overnight. The solvent was then evaporated under vacuum and the residue partitioned between ethyl acetate and water. The organic solution was separated and dried with magnesium sulphate, filtered and the solvent evaporated to give the title compound as an orange oil (1.28 g). 1H NMR δ (ppm) (CHCl3-d): 7.9 (s, 1H), 7.2 (s, 1H), 4.3 (q, 2H), 2.8 (m, 1H), 2.1 (m, 2H), 1.9 (m, 2H), 1.7-1.2 (m, 9H).

Workup

  1. stirringthe resulting solution stirred overnight
  2. customThe solvent was then evaporated under vacuum
  3. customthe residue partitioned between ethyl acetate and water
  4. customThe organic solution was separated
  5. dry with materialdried with magnesium sulphate
  6. filtrationfiltered
  7. customthe solvent evaporated

Sources & evidence

ORD record
ord-2e5ecd95568840c599f1b4502724cd7f
Source dataset
uspto-grants-2013_01
Patent number
US08362008B2

Reaction notes

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