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Dabco → N,N-dimethyl-3-methoxyimino-2-[(methylcarbamoyl)oximino]butyramide

HRID 26711
Notes
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Reaction equation

HRID 26711 reaction equation
[CH3:1][N:2]([CH3:13])[C:3](=[O:12])[C:4](=[N:10][OH:11])[C:5](=[N:7][O:8][CH3:9])[CH3:6].[CH3:14][N:15]=[C:16]=[O:17].C1N2CCN(CC2)C1>C(Cl)Cl>[CH3:13][N:2]([CH3:1])[C:3](=[O:12])[C:4](=[N:10][O:11][C:16](=[O:17])[NH:15][CH3:14])[C:5](=[N:7][O:8][CH3:9])[CH3:6]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 9237DabcoHCID 12228Methyl IsocyanateHCID 136099002N,N-dimethyl-2-hydroxyimino-3-methoxyiminobutyramide

Product 1

HCID 53959603N,N-dimethyl-3-methoxyimino-2-[(methylcarbamoyl)oximino]butyramide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 34 parts of N,N-dimethyl-2-hydroxyimino-3-methoxyiminobutyramide, 350 parts of methylene chloride, 13 parts of methyl isocyanate and one-tenth part triethylenediamine was stirred at 25° C. for 3 hours and then refluxed for 1 hour. The solvent was removed by stripping under reduced pressure (15 mm.) at 50° bath temperature, thereby affording the solid crude product. Recrystallization from a benzene-acetonitrile mixture gave 32 parts of N,N-dimethyl-3-methoxyimino-2-[(methylcarbamoyl)oximino]butyramide, m.p. 172°-173° C.

Workup

  1. temperaturerefluxed for 1 hour
  2. customThe solvent was removed
  3. customby stripping under reduced pressure (15 mm.) at 50°
  4. customaffording the solid crude product
  5. customRecrystallization from a benzene-acetonitrile mixture

Sources & evidence

ORD record
ord-515cd4a944c94100a0ce420c1a056260
Source dataset
uspto-grants-1979_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04151296

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes