Acetic Acid → {1-Methoxy-6-[(triphenylmethyl)amino]hexylidene}propanedinitrile

HRID 1416385Notes

Reaction equation

HRID 1416385 reaction equation
[C:1]([NH:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26](=[C:28]([C:31]#[N:32])[C:29]#[N:30])[OH:27])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+](=[CH2:35])=[N-].C(O)(=O)C>CCOCC.ClCCl>[C:1]([NH:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26](=[C:28]([C:29]#[N:30])[C:31]#[N:32])[O:27][CH3:35])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 9550DiazomethaneHCID 15406052HCID 15406052, compound

Product 1

HCID 15406053{1-Methoxy-6-[(triphenylmethyl)amino]hexylidene}propanedinitrile

Reagents, catalysts & solvents 1

HCID 21881112Ethyl ether methylene chlorideSolvent

Procedure

A suspension of the malononitrile of Example 2 (13 g, 31 mmole) in ether/dichloromethane (900 mL/100 mL), cooled in an ice bath, was treated with a freshly prepared ethereal solution of diazomethane (from 50 mmole of DiazaldR (Aldrich Chemical Company)). The solution was stirred for 6 hours and then neutralized with acetic acid (10 mL). The solution was evaporated to dryness and the residue chromatographed on silica gel using dichloromethane/acetone (4/1) as the eluent. Fractions containing product were pooled and evaporated to a syrup. The syrup was triturated with dichloromethane to induce crystallization. The crystals were filtered an dried to give 8.3 g (61%) of chromatographically pure product, useful as an intermediate compound.

Workup

  1. temperaturecooled in an ice bath
  2. customThe solution was evaporated to dryness
  3. customthe residue chromatographed on silica gel
  4. additionFractions containing product
  5. customevaporated to a syrup
  6. customThe syrup was triturated with dichloromethane
  7. customcrystallization
  8. filtrationThe crystals were filtered
  9. customan dried
  10. customto give 8.3 g (61%) of chromatographically pure product

Sources & evidence

ORD record
ord-eb42a91f766043d7a2a663238113fae3
Source dataset
uspto-grants-1999_06
Patent number
US05912340

Reaction notes

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