(Isocyanoimino)triphenylphosphorane → N-(2-(1,3,4-oxadiazol-2-yl)thiophen-3-yl)-2-(naphthalen-1-yl)acetamide

HRID 2098157Notes

Reaction equation

HRID 2098157 reaction equation
[N+:1]([N:3]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)#[C-:2].[C:23]1([CH2:33][C:34]([NH:36][C:37]2[CH:41]=[CH:40][S:39][C:38]=2[C:42]([OH:44])=O)=[O:35])[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][CH:24]=1>C(Cl)Cl>[O:44]1[CH:2]=[N:1][N:3]=[C:42]1[C:38]1[S:39][CH:40]=[CH:41][C:37]=1[NH:36][C:34](=[O:35])[CH2:33][C:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 11266621(Isocyanoimino)triphenylphosphoraneHCID 687556233-(2-(Naphthalen-1-yl)acetamido)thiophene-2-carboxylic acid

Product 1

HCID 46869071N-(2-(1,3,4-oxadiazol-2-yl)thiophen-3-yl)-2-(naphthalen-1-yl)acetamideYield 12.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (isocyanoimino)triphenylphosphorane (978 mg, 3.24 mmol) in anhydrous CH2Cl2 (30 mL) was added dropwise a solution of 3-(2-(naphthalen-1-yl)acetamido)thiophene-2-carboxylic acid (340 mg, 1.09 mmol) in anhydrous CH2Cl2 (27 mL). The resulting mixture was stirred at room temperature under nitrogen overnight and evaporated under reduced pressure. Purification by flash chromatography (silica, 30:70 ethyl acetate/hexane) gave N-(2-(1,3,4-oxadiazol-2-yl)thiophen-3-yl)-2-(naphthalen-1-yl)acetamide (45 mg, 12%). Method [7] m/z 357.9 (M+Na); retention time=5.919. 1H-NMR (CDCl3) δ 8.18 (d, J=1.1 Hz, 1H), 8.16 (d, J=1.4 Hz, 1H), 8.05 (d, J=8.3 Hz, 1H), 7.88 (d, J=8.0 Hz, 2H), 7.61-7.41 (m, 5H), 4.27 (s, 2H).

Workup

  1. customevaporated under reduced pressure
  2. customPurification by flash chromatography (silica, 30:70 ethyl acetate/hexane)

Sources & evidence

ORD record
ord-fd99f918c5b44bcab991765918e6ec0f
Source dataset
uspto-grants-2013_05
Patent number
US08450363B2

Reaction notes

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