Ethyl isocyanate → HCID 66887804, compound

HRID 2089051Notes

Reaction equation

HRID 2089051 reaction equation
FC(F)(F)C(O)=O.[I:8][C:9]1[C:17]2[C:12](=[N:13][CH:14]=[C:15]([NH2:18])[CH:16]=2)[N:11]([S:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)(=[O:21])=[O:20])[CH:10]=1.C(N(CC)CC)C.[CH2:35]([N:37]=[C:38]=[O:39])[CH3:36]>ClCCl>[CH2:35]([NH:37][C:38]([NH:18][C:15]1[CH:16]=[C:17]2[C:9]([I:8])=[CH:10][N:11]([S:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)(=[O:21])=[O:20])[C:12]2=[N:13][CH:14]=1)=[O:39])[CH3:36]

Participants

5

Reactant 3

HCID 8022Ethyl isocyanateHCID 8471TriethylamineHCID 66887602HCID 66887602, compound

Product 1

HCID 66887804HCID 66887804, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of Example 226a (120 mg, 0.234 mmol) in 5 mL dichloromethane was added triethylamine (0.326 mL, 2.34 mmol) followed by addition of ethyl isocyanate (0.074 mL, 0.935 mmol). The reaction mixture was stirred 16 hours at room temperature and then concentrated to dryness. The residue was partitioned with sodium bicarbonate solution and ethyl acetate. The organics were concentrated to dryness and the residue purified by silica gel flash chromatography eluting with 15% ethyl acetate, 85% dichloromethane to give the title compound as a pink-brown powder in quantitative yield. MS (ESI+) m/z 471.0 (M+H)+.

Workup

  1. concentrationconcentrated to dryness
  2. customThe residue was partitioned with sodium bicarbonate solution and ethyl acetate
  3. concentrationThe organics were concentrated to dryness
  4. customthe residue purified by silica gel flash chromatography
  5. washeluting with 15% ethyl acetate, 85% dichloromethane

Sources & evidence

ORD record
ord-1f92c78d568a47f3959120a32db57f7f
Source dataset
uspto-grants-2013_05
Patent number
US08435980B2

Reaction notes

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