Triethylamine → HCID 53837822, compound

HRID 1461213Notes

Reaction equation

[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][N:8]([CH3:27])[C:9]1[CH:26]=[CH:25][C:12]([CH:13]=[CH:14][C:15]2[CH:20]=[CH:19][C:18]([S:21]([CH3:24])(=[O:23])=[O:22])=[CH:17][CH:16]=2)=[CH:11][CH:10]=1.C(N(CC)CC)C.[C:35](Cl)(=[O:38])[CH:36]=[CH2:37]>ClCCl>[C:35]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][N:8]([CH3:27])[C:9]1[CH:26]=[CH:25][C:12]([CH:13]=[CH:14][C:15]2[CH:16]=[CH:17][C:18]([S:21]([CH3:24])(=[O:23])=[O:22])=[CH:19][CH:20]=2)=[CH:11][CH:10]=1)(=[O:38])[CH:36]=[CH2:37]

Participants

Conditions

Temperature: 23 °C

Procedure

A stirred mixture of 4'-[(6-hydroxyhexyl)-methylamino]-4-methylsulfonylstilbene (App-Ex. 4, 20.0 g, 52 mmol), triethylamine (6.3 g, 62 mmol) and dry dichloromethane (DCM) was treated dropwise with acryloyl chloride (5.6 g, 62 mmol) in 50 mL of DCM at 23° C. under nitrogen. The resulting solution was stirred at 23° C. for 72 hours, and then filtered. The filtrate was washed successively with saturated NaCl, with saturated NHCO3, and with water. The organic layer was dried (MgSO4), and the solvent was removed at reduced pressure to deposit a yellow oil which gradually crystallized. The product was recrystallized from tetrahydrofuran (THF)/hexanes to yield 15.5 g (68%) of a yellow solid, mp 88°-90° C.

Workup

filtrationfiltered
washThe filtrate was washed successively with saturated NaCl, with saturated NHCO3
dry with materialThe organic layer was dried (MgSO4)
customthe solvent was removed at reduced pressure
customgradually crystallized
customThe product was recrystallized from tetrahydrofuran (THF)/hexanes

Sources & evidence

ORD record: ord-6d3a867a31f54dfdaba4ea665e039703
Source dataset: uspto-grants-1991_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05075043

Reaction notes

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