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Potassium Carbonate → 5-Butoxy-2-cyanothiophen-3-yl dimethyl phosphate

HRID 263036
Notes
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Reaction equation

HRID 263036 reaction equation
C(=O)([O-])[O-].[K+].[K+].[P:7](Cl)([O:11][CH3:12])([O:9][CH3:10])=[O:8].[C:14]([C:16]1[S:17][C:18]([O:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:19][C:20]=1[OH:21])#[N:15]>C(#N)C>[C:14]([C:16]1[S:17][C:18]([O:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:19][C:20]=1[O:21][P:7]([O:11][CH3:12])([O:9][CH3:10])=[O:8])#[N:15]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 101863Phosphorochloridic acid, dimethyl esterHCID 213179005-Butoxy-3-hydroxythiophene-2-carbonitrile

Product 1

HCID 213179045-Butoxy-2-cyanothiophen-3-yl dimethyl phosphateYield 76.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
20 °C

Procedure

7.7 g of potassium carbonate and 7.7 g of O,O-dimethyl chlorophosphate were added to a solution of 11 g of 2-cyano-3-hydroxy-5-n-butoxy-thiophene in 150 ml of acetonitrile and the mixture was stirred for 16 hours at 20° C. and was filtered. The filtrate was evaporated to dryness under reduced pressure and the residue was dissolved in ether. The ether solution was washed with water containing 100 g/l of sodium chloride and then with 0.1 N sodium hydroxide solution containing 100 g/l of sodium chloride. The ether phase was dried and treated with activated carbon, filtered and concentrated to dryness to obtain 12.5 g of 2-cyano-3-(dimethoxyphosphoryloxy)-5-n-butoxy-thiophene with a refractive index of nD20 =1.511.

Workup

  1. filtrationwas filtered
  2. customThe filtrate was evaporated to dryness under reduced pressure
  3. dissolutionthe residue was dissolved in ether
  4. washThe ether solution was washed with water containing 100 g/l of sodium chloride
  5. additionwith 0.1 N sodium hydroxide solution containing 100 g/l of sodium chloride
  6. dry with materialThe ether phase was dried
  7. additiontreated with activated carbon
  8. filtrationfiltered
  9. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-1928049dd38644a09c5790389ad6f9ba
Source dataset
uspto-grants-1979_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04155996

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes