Triethylamine → O-ethyl O-(2-anthryl) S-propyl phosphorothioate

HRID 1632216Notes

Reaction equation

[CH:1]1[C:14]2[C:5](=[CH:6][C:7]3[C:12]([CH:13]=2)=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][C:2]=1[OH:15].C(N(CC)CC)C.[P:23](=[O:32])(Cl)([S:27][CH2:28][CH2:29][CH3:30])[O:24][CH2:25][CH3:26].C(OCC)(=O)C>C1(C)C=CC=CC=1>[P:23](=[O:32])([S:27][CH2:28][CH2:29][CH3:30])([O:15][C:2]1[CH:3]=[CH:4][C:5]2[C:14](=[CH:13][C:12]3[C:7]([CH:6]=2)=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH:1]=1)[O:24][CH2:25][CH3:26]

Participants

Conditions

Temperature: 0 °C

Procedure

2-Anthrol (3.0 grams; 0.015 mole), triethylamine (2.1 ml) and toluene (50 ml) were charged into a glass reaction vessel equipped with a mechanical stirrer and thermometer. The mixture was cooled to about 0° C. and O-ethyl S-propyl phosphorochloridothioate (3.01 grams; 0.015 mole) dissolved in toluene (38 ml) was added with stirring over a period of about 1/2 hour. After the addition was completed stirring was continued at room temperature overnight. After this time the reaction mixture was filtered to remove triethylamine hydrochloride and the filtrate stripped of solvent leaving solid residue. This residue was subjected to flash chromatography using ethyl acetate as the eluant to yield the desired product O-ethyl O-(2-anthryl) S-propyl phosphorothioate as a light tan solid melting at 79° to 83° C.

Workup

customequipped with a mechanical stirrer
additionwas added
additionAfter the addition
stirringwas completed stirring
waitwas continued at room temperature overnight
filtrationAfter this time the reaction mixture was filtered
customto remove triethylamine hydrochloride
customleaving solid residue

Sources & evidence

ORD record: ord-5bcafa2e160f425ba323e349694c32c5
Source dataset: uspto-grants-1984_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04474776

Reaction notes

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