Acetonitrile → 4-Amino-4'-propylazobenzene

HRID 881791

Reaction equation

HRID 881791 reaction equation
N[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]=[N:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.CCN(C(C)C)[CH:19]([CH3:21])[CH3:20].CC#[N:27]>CN(C=O)C>[NH2:27][C:6]1[CH:5]=[CH:4][C:3]([N:8]=[N:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:20][CH2:19][CH3:21])=[CH:12][CH:11]=2)=[CH:2][CH:7]=1

Participants

5

Reactant 3

HCID 6342Acetonitrile2×HCID 76077Benzenamine, 2-(2-phenyldiazenyl)-HCID 81531Diisopropylethylamine

Product 1

HCID 235134084-Amino-4'-propylazobenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of the aminoazobenzene (1 eq) and DIPEA (2 eq) in 1:1 MeCN:DMF at 0° C. was added 2-triethylammonium acetic acid chloride chloride8 (1.5 eq) in 1:1 MeCN:DMF and stirred for 15 min, then warmed to ambient temperature and stirred for 1-12 h at which time the solvent was removed in vacuo for purification by reverse phase silica gel chromatography (0.1% formic acid in H2O, gradient up to 50% MeCN: 0.1% formic acid in H2O).

Workup

  1. customwas removed in vacuo for purification by reverse phase silica gel chromatography (0.1% formic acid in H2O, gradient up to 50% MeCN: 0.1% formic acid in H2O)

Sources & evidence

ORD record
ord-6485a541c44e4403a60b8eb8b2530f9f
Source dataset
uspto-grants-2015_03
Patent number
US08993736B2

Linked notes

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