Methyl Isocyanate → HCID 53719918, compound

HRID 464644Notes

Reaction equation

HRID 464644 reaction equation
[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[C:3](=[N:8][OH:9])[S:2]2.[CH3:10][N:11]=[C:12]=[O:13]>C(Cl)Cl>[CH3:10][NH:11][C:12]([O:9][N:8]=[C:3]1[CH:4]2[CH2:7][CH:1]([CH2:6][CH2:5]2)[S:2]1)=[O:13]

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 71415463N-2-Thiabicyclo[2.2.1]heptan-3-ylidenehydroxylamine

Product 1

HCID 53719918HCID 53719918, compoundYield 98.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 6.6 g (0.046 m) of 2-thiabicyclo[2.2.1]heptan-3-one oxime, 2.9 g (0.05 m) of methyl isocyanate, and 60 ml of methylene chloride was stirred at room temperature for 17 hours. Removal of solvent gave 9.1 g of yellow-tan solid which was purified by dry column chromatography on silica gel using ether-acetone as eluent. There was obtained 5.2 g of the title product as a cream colored solid, m. 121°-2° C.

Workup

  1. customRemoval of solvent

Sources & evidence

ORD record
ord-55d5f01da4634c09acceb2294d5d2f50
Source dataset
uspto-grants-1985_10
Patent number
US04548929

Reaction notes

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