Methyl iodide → HCID 178503520, compound

HRID 1485358Notes

Reaction equation

HRID 1485358 reaction equation
C([O:3][C:4]([CH:6]1[C:12](=O)[CH2:11][CH2:10][N:9]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:8][CH2:7]1)=O)C.CC[O-].[Na+].[NH2:25][C:26]([NH2:28])=[S:27].[CH3:29]I>CCO>[C:17]([O:16][C:14]([N:9]1[CH2:8][CH2:7][C:6]2[C:4]([OH:3])=[N:25][C:26]([S:27][CH3:29])=[N:28][C:12]=2[CH2:11][CH2:10]1)=[O:15])([CH3:20])([CH3:19])[CH3:18]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 2723790ThioureaHCID 2723922Sodium ethoxideHCID 44365701-tert-Butyl 4-ethyl 5-oxoazepane-1,4-dicarboxylate

Product 1

HCID 178503520HCID 178503520, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To solution of 5-oxo-azepane-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester (10.5 g, 0.04 mol) in EtOH (168 mL) was added NaOEt (8.1 g, 0.12 mol) and thiourea (4.2 g, 0.06 mol). The mixture was heated at reflux for 12 h. The mixture was cooled, treated with MeI (3.0 mL, 0.05 mol) drop-wise, and stirred at rt for 1 h. The mixture was concentrated and the residue was dissolved in water and acidified to pH=7 with HOAc (a precipitate formed). The solid was filtered to give the title compound (8.4 g, 73%), which was used in the next step without further purification.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 12 h
  3. temperatureThe mixture was cooled
  4. concentrationThe mixture was concentrated
  5. dissolutionthe residue was dissolved in water
  6. customformed)
  7. filtrationThe solid was filtered

Sources & evidence

ORD record
ord-5fa32e53426740d694b2788ca6c44718
Source dataset
uspto-grants-2016_08
Patent number
US09422293B2

Reaction notes

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