Hydrochloric Acid → HCID 69278463, compound

HRID 1619744Notes

Reaction equation

HRID 1619744 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]=[C:12]=[O:13])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:14]1([C:20]2[CH2:24][C:23]3([CH2:28][CH2:27][NH:26][CH2:25]3)[O:22][N:21]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(N(CC)CC)C.Cl>C1COCC1>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([N:26]2[CH2:27][CH2:28][C:23]3([O:22][N:21]=[C:20]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[CH2:24]3)[CH2:25]2)=[O:13])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 27356951-Tert-butyl-4-isocyanatobenzeneHCID 59830389HCID 59830389, compound

Product 1

HCID 69278463HCID 69278463, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Tert-butylphenyl isocyanate (350 mg, 2 mmol) was added to a solution of compound R (420 mg crude product, approx. 2 mmol) in abs. THF (20 ml) under argon at RT within 10 min. After 1 h the cloudy solution was mixed with triethylamine (0.3 ml, 2.22 mmol). The reaction mixture was stirred for a further 2 h and then mixed with 2 N HCl solution (10 ml). The acidic reaction mixture was stirred for 10 min and then extracted with EtOAc (3×20 ml). The combined organic phases were washed with sat. Na2HCO3 solution (10 ml), dried over Na2SO4 and concentrated to dryness under vacuum. The residue was recrystallised from toluene (15 ml). The desired product N-(4-tert-butylphenyl)-3-phenyl-1-oxa-2,7-diazaspiro[4.4]non-2-ene-7-carboxamide was thus obtained in a yield of 415 mg (55%) having a melting point of 207-208° C. (from EtOH, crystal transformation between 183 and 188° C.).

Workup

  1. stirringThe acidic reaction mixture was stirred for 10 min
  2. extractionextracted with EtOAc (3×20 ml)
  3. washThe combined organic phases were washed with sat. Na2HCO3 solution (10 ml)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to dryness under vacuum
  6. customThe residue was recrystallised from toluene (15 ml)

Sources & evidence

ORD record
ord-c89e99cb9f0843159d3121652d384e99
Source dataset
uspto-grants-2014_07
Patent number
US08772307B2

Reaction notes

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