Triphenylphosphine → HCID 18404100, compound

HRID 1017719Notes

Reaction equation

HRID 1017719 reaction equation
[N:1]([C:4]1[CH:8]=[CH:7][S:6][C:5]=1[CH:9]=[O:10])=[N+]=[N-].[C:11]1([P:17]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C1COCC1>[C:24]1([P:17](=[N:1][C:4]2[CH:8]=[CH:7][S:6][C:5]=2[CH:9]=[O:10])([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 4155502HCID 4155502, compound

Product 1

HCID 18404100HCID 18404100, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-azido-2-thiophenecarbaldehyde (11-1, 1.00 g, 6.53 mmol, 1 equiv, prepared by the method of Gronowitz, S., Westerlund, C., and Hornfeldt, A.-B. Acta. Chem. Scand. B 1975, 29, 224-232) and triphenylphosphine (1.71 g, 6.53 mmol, 1.00 equiv) in THF (30 mL) was stirred at 23° C. for 6 h. The reaction mixture was concentrated to give 3-[(triphenylphosphoranylidene)amino]-2-thiophenecarbaldehyde (11-2). 1H NMR (400 MHz, CD3OD) δ 10.35 (s, 1H), 7.72 (m, 6H), 7.58 (m, 2H), 7.49 (m, 6H), 7.27 (dd, 1H, J=4.5, 0.8 Hz), 6.09 (d, 1H, J=4.5 Hz).

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-b9dcae17f18540229ba7b65fa84d73a0
Source dataset
uspto-grants-2002_11
Patent number
US06479512B1

Reaction notes

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