1,1'-Carbonyldiimidazole → Nitrogen

HRID 1938666Notes

Reaction equation

HRID 1938666 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:13]([N:25]1[N:29]=[N:28][C:27]([CH2:30][C:31]([OH:33])=[O:32])=[N:26]1)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]>C1COCC1>[CH2:13]([N:25]1[N:29]=[N:28][C:27]([CH2:30][C:31]([OH:33])=[O:32])=[N:26]1)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].[N:25]#[N:26]

Participants

5

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 10661649HCID 10661649, compound

Product 2

HCID 947NitrogenHCID 10661649HCID 10661649, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Carbonyldiimidazole (5.74 g, 0.035 mol) was added to a solution of the 2-dodecyltetrazole acetic acid (10.0 g, 0.034 mol) obtained in (c) above in dry THF (100 mL) under an inert atmosphere (N2). The mixture was stirred at room temperature for 30 minutes, then 2,6-diisopropylaniline (6.7 mL, 0.038 mol) was added in one portion. The resulting solution was stirred for 3 days at room temperature, concentrated in vacuo, taken up in dichloromethane (200 mL), washed with water (100 mL) and brine (100 mL), and dried over Na2SO4. The dried solution was filtered, concentrated, and chromatographed on silica gel, eluting with 15% ethyl acetate in hexanes to give 10.6 g, 68% of the title compound as an off-white solid, mp 75°-79° C.

Sources & evidence

ORD record
ord-df19ac39c5fe417795ac860fed75bf48
Source dataset
uspto-grants-1997_12
Patent number
US05693657

Reaction notes

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