Methyl fluorosulfate → HCID 12370270, compound

HRID 2083030Notes

Reaction equation

HRID 2083030 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:13]=[CH:12][C:11](=[O:14])[CH:10]=[CH:9]2)=[CH:4][CH:3]=1.[F:15][S:16]([O:19][CH3:20])(=[O:18])=[O:17]>C(COC)OC>[F:15][S:16]([O-:19])(=[O:18])=[O:17].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]2[CH:9]=[CH:10][C:11]([O:14][CH3:20])=[CH:12][CH:13]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 9870Methyl fluorosulfateHCID 759442HCID 759442, compound

Product 1

HCID 12370270HCID 12370270, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of 18.7 g. (0.091 mole) of dried 1-(4-chlorophenyl)-4(1H)-pyridinone [prepared by the process set forth in D. Vorlander, Ber., 58, 1908 (1925)] in 160 ml. of dimethoxyethane was heated to reflux. Without further external heating, 14.2 g. (0.123 mole) of methyl fluorosulfonate was added gradually. The mixture boiled vigorously during the addition and crystalline product started to separate. After the addition was complete, the mixture was stirred at room temperature for 1 hour and then cooled to 10° C. The product was collected by filtration, washed with cold dimethoxyethane and ether and dried in vacuo: yield 28.0 g. (96.5%); m.p. 182°-185° C.; NMR (DMSO-d6) δ4.26 (s, 3H, CH3O), 6.27 (d, 2H, β-pyridyl H), 6.32 (s, 4H, aromatics), 7.62 (d, 2H, α-pyridyl H). The elemental analyses for C, H, N and Cl were within ±0.4 % of the theoretical values.

Workup

  1. additionThe mixture boiled vigorously during the addition and crystalline product
  2. customto separate
  3. additionAfter the addition
  4. temperaturecooled to 10° C
  5. filtrationThe product was collected by filtration
  6. washwashed with cold dimethoxyethane and ether
  7. customdried in vacuo

Sources & evidence

ORD record
ord-355d3d15ebad46c089ee9260c98f72ce
Source dataset
uspto-grants-1978_04
Patent number
US04083984

Reaction notes

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