Potassium Carbonate → 2-Cyano-3-(diethoxythiophosphoryloxy)-5-ethylthio-thiophene

HRID 65585

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[P:7](Cl)([O:12][CH2:13][CH3:14])([O:9][CH2:10][CH3:11])=[S:8].[C:16]([C:18]1[S:19][C:20]([S:24][CH2:25][CH3:26])=[CH:21][C:22]=1[OH:23])#[N:17]>C(#N)C>[C:16]([C:18]1[S:19][C:20]([S:24][CH2:25][CH3:26])=[CH:21][C:22]=1[O:23][P:7]([O:12][CH2:13][CH3:14])([O:9][CH2:10][CH3:11])=[S:8])#[N:17]

Participants

Conditions

Temperature: 20 °C

Procedure

7 g of potassium carbonate and 9.4 g of O,O-diethyl chlorothiophosphate were added to a solution of 9.3 g of 2-cyano-3-hydroxy-5-ethylthio-thiophene in 150 ml of acetonitrile and the mixture was stirred for 24 hours at 20° C. and was filtered. The filtrate was evaporated to dryness and the residue was chromatographed over silica gel. Elution with an 8-2 cyclohexane-ethyl acetate mixture yielded 14.6 g of 2-cyano-3-(diethoxythiophosphoryloxy)-5-ethylthio-thiophene with a refractive index of nD20 = 1.5635.

Workup

filtrationwas filtered
customThe filtrate was evaporated to dryness
customthe residue was chromatographed over silica gel
washElution with an 8-2 cyclohexane-ethyl acetate mixture

Sources & evidence

ORD record: ord-e62d9c3939ae42bf9f760fd70880f123
Source dataset: uspto-grants-1978_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04128562

Linked notes

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