Tetrahydrofuran → HCID 86733939, compound

HRID 1576227Notes

Reaction equation

HRID 1576227 reaction equation
[C:1]([C:3](=[N:7][O:8][CH3:9])[C:4]([NH2:6])=[O:5])#[N:2].O1CCCC1.[H-].[Na+].[CH3:17][O:18][CH2:19][N:20]=[C:21]=[O:22]>C(O)(=O)C>[C:1]([C:3](=[N:7][O:8][CH3:9])[C:4]([NH:6][C:21](=[O:22])[NH:20][CH2:19][O:18][CH3:17])=[O:5])#[N:2]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 62609Methoxymethyl isocyanateHCID 534247972-Cyano-2-(methoxyimino)acetamide

Product 1

HCID 86733939HCID 86733939, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a suspension of 2.70 g. of 2-cyano-2-methoxyiminoacetamide in 10 ml. of tetrahydrofuran was added 1.20 g. of a 55% suspension of sodium hydride in mineral oil in portions with stirring. After stirring for 15 minutes, 2.40 g. of methoxymethylisocyanate was added dropwise. The mixture was stirred at 50°C. for 3 minutes to ensure completion of the reaction. The mixture was then cooled in an ice bath, and a solution of 1.9 ml. of acetic acid in 120 ml. of ice water was added rapidly with stirring. After stirring for another 25 minutes, 2-cyano-2-methoxyimino-N-methoxymethylcarbamoylacetamide was collected on a filter, washed with water and ether, and dried. The product weighed 2.7 g. and melted at 163.5°-165°C.

Workup

  1. additionTo a suspension of 2.70 g
  2. stirringThe mixture was stirred at 50°C. for 3 minutes
  3. customcompletion of the reaction
  4. temperatureThe mixture was then cooled in an ice bath
  5. stirringwith stirring
  6. stirringAfter stirring for another 25 minutes
  7. custom2-cyano-2-methoxyimino-N-methoxymethylcarbamoylacetamide was collected on a filter
  8. washwashed with water and ether
  9. customdried

Sources & evidence

ORD record
ord-c7bdc9d660c84528862c1908ae69f997
Source dataset
uspto-grants-1976_09
Patent number
US03979518

Reaction notes

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