Triethyl phosphite → HCID 14874066, compound

HRID 1774082Notes

Reaction equation

Br[CH2:2][C:3]1[C:4]2[C:9]([N:10]=[C:11]3[C:16]=1[CH:15]=[CH:14][CH:13]=[CH:12]3)=[CH:8][CH:7]=[CH:6][CH:5]=2.[P:17]([O:24]CC)([O:21][CH2:22][CH3:23])[O:18][CH2:19][CH3:20]>>[CH:5]1[C:4]2[C:9](=[N:10][C:11]3[C:16]([C:3]=2[CH2:2][P:17](=[O:24])([O:21][CH2:22][CH3:23])[O:18][CH2:19][CH3:20])=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:8]=[CH:7][CH:6]=1

Participants

Reactant 2

HCID 31215Triethyl phosphite

HCID 1509309-Bromomethylacridine

Product 1

HCID 14874066HCID 14874066, compoundYield 94%

Procedure

The mixture of 10 (1.5 g, 5.5 mmol) and triethyl phosphite (2 mL) was heated to reflux for 4 h. After cooling down to room temperature, the excess triethyl phosphite was removed under vacuum to afford 11 (1.7 g) in 94% yield. 1H NMR (400 MHz, CDCl3) δ 8.23 (d, J=8.8 Hz, 2H), 8.17 (d, J=8.8 Hz, 2H), 7.72 (t, J=7.2 Hz, 2H), 7.54 (t, J=7.2 Hz, 2H), 4.13 (d, J=24 Hz, 2H), 3.92-3.77 (m, 4H), 1.04 (t, J=7.2 Hz, 6H). 13C NMR (400 MHz, CDCl3) δ 148.4, 148.3, 135.8, 135.7, 129.9, 129.8, 125.8, 125.3, 125.2, 124.9, 124.8, 62.4, 27.5, 26.1, 16.1.

Workup

temperaturewas heated
temperatureto reflux for 4 h
customthe excess triethyl phosphite was removed under vacuum

Sources & evidence

ORD record: ord-42d38f3434e548509281100fc70170eb
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09255933B2

Reaction notes

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