Tributylamine → Methyl 5[4-(benzenesulfonyl)-1-piperazinyl]benzofuran-2-carboxylate

HRID 628793Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]([O:12][CH3:13])=[O:11])=[CH:7][C:6]=2[CH:14]=1.[C:15]1([S:21]([N:24]([CH2:28][CH2:29]Cl)[CH2:25][CH2:26]Cl)(=[O:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(N(CCCC)CCCC)CCC>CO>[C:15]1([S:21]([N:24]2[CH2:28][CH2:29][N:1]([C:2]3[CH:3]=[CH:4][C:5]4[O:9][C:8]([C:10]([O:12][CH3:13])=[O:11])=[CH:7][C:6]=4[CH:14]=3)[CH2:26][CH2:25]2)(=[O:23])=[O:22])[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

Conditions

Temperature: 75 °C

Procedure

Methyl 5-aminobenzofuran-2-carboxylate (200 g) and N-benzenesulfonyl-N,N-bis(2-chloroethyl)amine (289 g) were added to tributyl amine (1012 ml) under stifling at 25-30° C. The resulting mixture was heated to 73-77° C., followed by stirring for 43 hours at the same temperature. The reaction mass was cooled to 25-30° C., followed by the addition of methanol (506 ml) and then stirring for 30 minutes at 25-30° C. The resulting mass was filtered, washed with chilled methanol (200 ml) and then dried to produce 220 g of methyl 5-[4-(benzenesulfonyl)-1-piperazinyl]benzofuran-2-carboxylate as a fine powder (Purity by HPLC: 99.5%).

Workup

customunder stifling at 25-30° C
temperatureThe reaction mass was cooled to 25-30° C.
stirringstirring for 30 minutes at 25-30° C
filtrationThe resulting mass was filtered
washwashed with chilled methanol (200 ml)
customdried

Sources & evidence

ORD record: ord-a77bf8e7dd2940d791f48c8e11edb982
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09315456B2

Reaction notes

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