Triphenylphosphine → 5-Chloro-N-{2-[3-(cyanomethoxy)benzyl]-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl}-2-thiophenecarboxamide

HRID 585501Notes

Reaction equation

HRID 585501 reaction equation
O[CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[O:6][CH2:7][C:8]#[N:9].[Cl:13][C:14]1[S:18][C:17]([C:19]([NH:21][C:22]2[CH:30]=[CH:29][CH:28]=[C:27]3[C:23]=2[C:24](=[O:32])[NH:25][C:26]3=[O:31])=[O:20])=[CH:16][CH:15]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[Cl:13][C:14]1[S:18][C:17]([C:19]([NH:21][C:22]2[CH:30]=[CH:29][CH:28]=[C:27]3[C:23]=2[C:24](=[O:32])[N:25]([CH2:2][C:3]2[CH:12]=[CH:11][CH:10]=[C:5]([O:6][CH2:7][C:8]#[N:9])[CH:4]=2)[C:26]3=[O:31])=[O:20])=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 41357405-Chloro-N-(1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl)thiophene-2-carboxamideHCID 113211372-[3-(Hydroxymethyl)phenoxy]acetonitrile

Product 1

HCID 99554965-Chloro-N-{2-[3-(cyanomethoxy)benzyl]-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl}-2-thiophenecarboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.46 g (8.94 mmol) of 2-[3-(hydroxymethyl)phenoxy]acetonitrile, 2.5 g (8.15 mmol) of 5-chloro-N-(1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl)-2-thiophenecarboxamide and 4.28 g (16.3 mmol) of triphenylphosphine are, under argon, dissolved in 250 ml of tetrahydrofuran. 2.84 g (16.3 mmol) of DEAD (diethyl azodicarboxylate) are added, and the mixture is stirred at room temperature overnight. 10 g of silica gel are added and the mixture is concentrated under reduced pressure and chromatographed on a silica gel column (gradient: toluene->toluene/ethyl acetate=4:1). This gives 2.37 g (64.4% of theory) of the target compound of melting point 164° C. Rf (SiO2, toluene/ethyl acetate=4:1): 0.45.

Workup

  1. addition10 g of silica gel are added
  2. concentrationthe mixture is concentrated under reduced pressure
  3. customchromatographed on a silica gel column (gradient: toluene->toluene/ethyl acetate=4:1)

Sources & evidence

ORD record
ord-bc527c4cec9d441caef6ea6a8c70ab6b
Source dataset
uspto-grants-2005_08
Patent number
US06933295B2

Reaction notes

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