P,P-Diphenylphosphinic azide → 4-Cyano-3-(2,4-dichlorophenyl)-5-morpholin-4-ylthiophene-2-carbonyl azide

HRID 572603Notes

Reaction equation

HRID 572603 reaction equation
[C:1]([C:3]1[C:4]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=2[Cl:24])=[C:5]([C:14](O)=[O:15])[S:6][C:7]=1[N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)#[N:2].C1(P([N:39]=[N+:40]=[N-:41])(C2C=CC=CC=2)=O)C=CC=CC=1>C1COCC1>[C:1]([C:3]1[C:4]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=2[Cl:24])=[C:5]([C:14]([N:39]=[N+:40]=[N-:41])=[O:15])[S:6][C:7]=1[N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)#[N:2]

Participants

4

Reactant 2

HCID 199401P,P-Diphenylphosphinic azideHCID 441556654-Cyano-3-(2,4-dichlorophenyl)-5-morpholin-4-ylthiophene-2-carboxylic acid

Product 1

HCID 866375454-Cyano-3-(2,4-dichlorophenyl)-5-morpholin-4-ylthiophene-2-carbonyl azideYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-cyano-3-(2,4-dichlorophenyl)-5-morpholin-4-ylthiophene-2-carboxylic acid (0.38 g, 0.99 mmol) and TEA (0.414 mL, 2.97 mmol) in anhydrous THF (15 mL) was added diphenylphosphoryl azide (0.341 mL, 1.58 mmol) in one portion, under nitrogen. The reaction mixture was allowed to stir at rt overnight, and was concentrated. The residue was purified by column chromatography to give 4-cyano-3-(2,4-dichlorophenyl)-5-morpholin-4-ylthiophene-2-carbonyl azide (0.318 g, 79%).

Workup

  1. concentrationwas concentrated
  2. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-8479d61ce00c4d53a1f626cebb12b57b
Source dataset
uspto-grants-2015_05
Patent number
US09029411B2

Reaction notes

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