Ethyl isocyanate → HCID 136660218, compound

HRID 1034966Notes

Reaction equation

HRID 1034966 reaction equation
[CH2:1]([O:8][C:9](=[O:40])[N:10]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27]2[C:31]([C:32]3[CH2:37][CH2:36][CH2:35][CH2:34][CH:33]=3)=[C:30]([NH2:38])[N:29]([CH3:39])[N:28]=2)[CH:22]=1)[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N=[C:44]=[O:45])C>N1C=CC=CC=1>[CH3:19][O:18][C:15]1[CH:14]=[CH:13][C:12]([CH2:11][N:10]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([C:27]3[C:31]4[C:32]5[CH2:37][CH2:36][CH2:35][CH2:34][C:33]=5[C:44](=[O:45])[NH:38][C:30]=4[N:29]([CH3:39])[N:28]=3)[CH:22]=2)[C:9](=[O:40])[O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 8022Ethyl isocyanateHCID 69476031HCID 69476031, compound

Product 1

HCID 136660218HCID 136660218, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of EXAMPLE 56E (3.8 g, 7.1 mmol) in pyridine (100 mL) was added ethyl isocyanate (1.6 mL, 21 mmol) and the solution stirred at ambient temperature for 24 hours. The mixture was heated at reflux overnight, cooled, concentrated and the residue purified by flash chromatography on silica gel using ethyl acetate to give 3.4 g (85%) of the title compound. MS (DCI): m/z 563 (M+H)+.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight
  3. temperaturecooled
  4. concentrationconcentrated
  5. customthe residue purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-ee5e146af16b4bc08ce5090d37b6076a
Source dataset
uspto-grants-2013_10
Patent number
US08546368B2

Reaction notes

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