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

HRID 2119259Notes

Reaction equation

HRID 2119259 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 Diazald® (Aldrich Chemical Company)). The solution was stirred for 6 hr 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 and 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. customdried
  10. customto give 8.3 g (61%) of chromatographically pure product

Sources & evidence

ORD record
ord-e93a3359b93d413f98a382239fd939cd
Source dataset
uspto-grants-2004_02
Patent number
USRE038416E1

Reaction notes

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