Diethyl Ether → HCID 54331633, compound

HRID 1415109Notes

Reaction equation

HRID 1415109 reaction equation
[N:1](=[C:3]1[C:8](=[O:9])[NH:7][CH2:6][CH2:5][S:4]1)[OH:2].[CH3:10][N:11]=[C:12]=[O:13].C(OCC)C.CCCCCC.[CH3:25][N:26]([CH:28]=[O:29])C>C(N(CC)CC)C>[CH3:10][NH:11][C:12]([N:7]1[CH2:6][CH2:5][S:4][C:3](=[N:1][O:2][C:28](=[O:29])[NH:26][CH3:25])[C:8]1=[O:9])=[O:13]

Participants

7

Reactant 5

HCID 3283Diethyl EtherHCID 6228DimethylformamideHCID 8058HexaneHCID 12228Methyl IsocyanateHCID 713661032-(Hydroxyimino)thiomorpholin-3-one

Product 1

HCID 54331633HCID 54331633, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineCatalyst

Procedure

To a solution of 4 g. (0.027 mole) of the oxime of Example I in 50 ml of DMF was added 3 g. (0.053 mole) of methyl isocyanate and 3 drops of triethylamine. This mixture was left in a pressure bottle over night at room temperature after which it was added with stirring to a 50:50 ethyl ether:hexane mixture (about 200 ml.). The resulting white solid was collected, washed thoroughly with ethyl ether and air dried. Recrystallization from acetonitrile produced 4 g. (57 per cent) of product, m.p. 187°-189° C.

Workup

  1. waitThis mixture was left in a pressure bottle over night at room temperature after which it
  2. additionwas added
  3. customThe resulting white solid was collected
  4. washwashed thoroughly with ethyl ether and air
  5. customdried
  6. customRecrystallization from acetonitrile
  7. customproduced 4 g

Sources & evidence

ORD record
ord-9f97475328844b97b1c3f0afd29e1be3
Source dataset
uspto-grants-1977_01
Patent number
US04003895

Reaction notes

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