Ethylenediamine → 7-Methoxy-1-benzothiophene-2-carbonitrile

HRID 2220315Notes

Reaction equation

I[C:2]1[S:3][C:4]2[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[CH:7][C:5]=2[CH:6]=1.[Cu][C:14]#[N:15].CN(C)C=O.C(N)CN>O.C1(C)C=CC=CC=1>[CH3:12][O:11][C:10]1[C:4]2[S:3][C:2]([C:14]#[N:15])=[CH:6][C:5]=2[CH:7]=[CH:8][CH:9]=1

Participants

Conditions

Temperature: 40 °C

Procedure

A solution of 2-iodo-7-methoxy-1-benzothiophene (10.0 g, 0.35 mol), copper (1) cyanide (6.17 g, 0.68 mol) and anhydrous N,N-dimethylformamide (40 mL) are warmed to 130° C. After 2.5 h at 130° C. no starting material is detectable as measured by HPLC at 220 nm. The reaction is cooled to 40° C. and a solution 25% v/v ethylenediamine in water (30 mL) and toluene (20 mL) are added. The mixture is stirred to room temperature. Additional toluene (30 mL) is added and the heterogeneous mixture is filtered. The layers of the mother liquors are separated and the aqueous layer is extracted with toluene (3×50 mL). The combined organic extracts were washed with water (2×50 mL), dried (MgSO4) and the solvent evaporated in vacuo to give the title compound (5.78 g, 88%), which was used without further purification; δH (300 MHz, CDCl3) 7.79 (1H, s, 3-ArH), 7.46-7.38 (1H, m, 4-ArH), 7.37-7.31 (1H, m, 5-ArH), 6.88-6.82 (1H, m, 6-ArH) and 3.94 (3H, s, OCH3).

Workup

filtrationthe heterogeneous mixture is filtered
customThe layers of the mother liquors are separated
extractionthe aqueous layer is extracted with toluene (3×50 mL)
washThe combined organic extracts were washed with water (2×50 mL)
dry with materialdried (MgSO4)
customthe solvent evaporated in vacuo

Sources & evidence

ORD record: ord-25717a7e751c4ea3abfda2abbfa8d577
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07417064B2

Reaction notes

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