Benzenesulfonyl chloride → [(2S)-3,8-dioxo-1,2-dihydro-3H,8H-2a,5,8a-triazaacenaphthylen-2-yl]methyl benzenesulfonate

HRID 420693Notes

Reaction equation

[OH:1][CH2:2][C@H:3]1[N:13]2[C:14]3[N:5]([C:6](=[O:16])[CH:7]=[CH:8][C:9]=3[N:10]=[CH:11][C:12]2=[O:15])[CH2:4]1.[C:17]1([S:23](Cl)(=[O:25])=[O:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CCN(CC)CC.CN(C)CCO>C(Cl)Cl.CC(OC)(C)C>[C:17]1([S:23]([O:1][CH2:2][C@H:3]2[N:13]3[C:14]4[N:5]([C:6](=[O:16])[CH:7]=[CH:8][C:9]=4[N:10]=[CH:11][C:12]3=[O:15])[CH2:4]2)(=[O:25])=[O:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 42 °C

Procedure

To the suspension of (2S)-2-(hydroxymethyl)-1,2-dihydro-3H,8H-2a,5,8a-triazaacenaphthylene-3,8-dione (26.5 g, 121 mmol) in DCM (320 ml) was added benzenesulfonyl chloride (23.38 ml, 181 mmol) followed by Et3N (39.6 ml, 284 mmol). The reaction mixture was heated at gentle reflux at 42° C. for 2 h. Then, the reaction was cooled to 5° C. and 2-(dimethylamino)ethanol (7.30 ml, 72.5 mmol) was added dropwise. The crude was stirred at room temperature for 30 min and TBME (600 ml) was added. The obtained solid was filtered. The resulting solid was suspended in 100 ml 1N HCl and washed with water and TBME, dried to give [(2S)-3,8-dioxo-1,2-dihydro-3H,8H-2a,5,8a-triazaacenaphthylen-2-yl]methyl benzenesulfonate (37.04 g, 85%) as a cream solid.

Workup

temperatureThe reaction mixture was heated
temperatureThen, the reaction was cooled to 5° C.
filtrationThe obtained solid was filtered
washwashed with water and TBME
customdried

Sources & evidence

ORD record: ord-b5175103a35c40f5ad84075cbb8cc60f
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08097628B2

Reaction notes

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