Methyl Isocyanate → 1-(Methylcarbamoyl)-3-[(4-chlorophenyl)thio]-azacycloheptan-2-one

HRID 358438

Reaction equation

HRID 358438 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH:9]2[CH2:15][CH2:14][CH2:13][CH2:12][NH:11][C:10]2=[O:16])=[CH:4][CH:3]=1.[CH3:17][N:18]=[C:19]=[O:20].C([O-])(=O)CCCCCCCCCCC.C([O-])(=O)CCCCCCCCCCC.C([Sn+2]CCCC)CCC>C1(C)C=CC=CC=1>[CH3:17][NH:18][C:19]([N:11]1[CH2:12][CH2:13][CH2:14][CH2:15][CH:9]([S:8][C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[C:10]1=[O:16])=[O:20]

Participants

5

Reactant 3

HCID 12228Methyl IsocyanateHCID 9809426Di-n-butyldilauryltinHCID 13268904HCID 13268904, compound

Product 1

HCID 204480031-(Methylcarbamoyl)-3-[(4-chlorophenyl)thio]-azacycloheptan-2-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

25.6 g (0.1 mol) of 3-[(4-chlorophenyl)thio]-azacycloheptan-2-one together with 5.7 g (0.1 mol) of methyl isocyanate and 100 mg of dibutyl-tin dilaurate in 150 ml of absolute toluene are boiled under reflux for 5 hours. After the mixture has cooled, the solvent is stripped off in vacuo, and the oily residue is used for further reactions.

Workup

  1. temperatureunder reflux for 5 hours
  2. temperatureAfter the mixture has cooled

Sources & evidence

ORD record
ord-7067370980904d529ab71b7ad55b6b99
Source dataset
uspto-grants-1984_08
Patent number
US04468392

Linked notes

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