Methanimidic acid, N-cyano-, ethyl ester → HCID 178423705, compound

HRID 621387Notes

Reaction equation

HRID 621387 reaction equation
[CH3:1][C:2]1([CH3:13])[CH2:11][CH2:10][CH:9]2[CH:4]([CH2:5][CH2:6][CH2:7][CH2:8]2)[CH:3]1[NH2:12].[C:14]([N:16]=[CH:17]OCC)#[N:15]>C(O)C>[C:14]([N:16]=[CH:17][NH:12][CH:3]1[CH:4]2[CH:9]([CH2:8][CH2:7][CH2:6][CH2:5]2)[CH2:10][CH2:11][C:2]1([CH3:13])[CH3:1])#[N:15]

Participants

4

Reactant 2

HCID 9920370Methanimidic acid, N-cyano-, ethyl esterHCID 21242528Decahydro-2,2-dimethyl-1-naphthalenamine

Product 1

HCID 178423705HCID 178423705, compoundYield 54.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred and heated (<40° C.) solution of 96 parts of decahydro-2,2-dimethyl-1-naphthalenamine in 400 parts of ethanol were added dropwise 48 parts of ethyl N-cyanomethanimidate. Upon complete addition, stirring was continued for 2 hours. The precipitated product was filtered off (and set aside) and the filtrate was evaporated. The residue was treated with 2,2'-oxybispropane. The precipitated product was filtered off and combined with the product, which was set aside (see above). Both were crystallized from acetonitrile. The product was filtered off and dried, yielding 67 parts (54.1%) of N'-cyano-N-(decahydro-2,2-dimethyl-1-naphthalenyl)methanimidamide; mp. 227.6° C. (intermediate 7).

Workup

  1. additionUpon complete addition
  2. stirringstirring
  3. filtrationThe precipitated product was filtered off (and
  4. customwas evaporated
  5. additionThe residue was treated with 2,2'-oxybispropane
  6. filtrationThe precipitated product was filtered off
  7. customBoth were crystallized from acetonitrile
  8. filtrationThe product was filtered off
  9. customdried

Sources & evidence

ORD record
ord-8cfbfa11a5bb482cb5ac25f80fe827d0
Source dataset
uspto-grants-1989_04
Patent number
US04824472

Reaction notes

Loading…