Ethyl isocyanate → HCID 11574496, compound

HRID 1432137Notes

Reaction equation

HRID 1432137 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][C:11]([C:13]([N:15]3[CH2:21][CH:20]4[N:22]([CH3:23])[CH:17]([CH2:18][CH2:19]4)[CH2:16]3)=[O:14])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[CH2:24]([N:26]=[C:27]=[O:28])[CH3:25].[OH-].[Na+]>CO>[CH2:24]([NH:26][C:27]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][C:11]([C:13]([N:15]3[CH2:21][CH:20]4[N:22]([CH3:23])[CH:17]([CH2:18][CH2:19]4)[CH2:16]3)=[O:14])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1)=[O:28])[CH3:25]

Participants

5

Reactant 3

HCID 8022Ethyl isocyanateHCID 14798Sodium HydroxideHCID 11681151HCID 11681151, compound

Product 1

HCID 11574496HCID 11574496, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of [5-(4-amino-phenyl)-furan-2-yl]-(8-methyl-3,8-diaza-bicyclo[3.2.1]oct-3-yl)-methanone (0.44 g, 1.41 mmol) and methanol (30 ml) was added: ethylisocyanate (291 mg, 4.08 mmol) at −50° C. and then allowed to reach room temperature. Aqueous sodium hydroxide (5 ml, 1M) was added and the mixture was extracted twice with dichloromethane (2×10 ml). Chromatography on silica gel with dichloromethane, 10% methanol and 1% aqueous ammonia as solvent gave the title compound. Yield 519 mg (96%). The corresponding salt was obtained by addition of a diethyl ether and methanol mixture (9:1) saturated with fumaric acid. Mp. 183.6-186.4° C.

Workup

  1. additionwas added
  2. customat −50° C.
  3. customto reach room temperature
  4. extractionthe mixture was extracted twice with dichloromethane (2×10 ml)

Sources & evidence

ORD record
ord-1bfcca45d0a641a3acdb74d40e33585b
Source dataset
uspto-grants-2009_11
Patent number
US07612074B2

Reaction notes

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