Ethylene Glycol → HCID 19595072, compound

HRID 486652Notes

Reaction equation

HRID 486652 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[C:20]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[O:28][CH3:29])=[C:19](Cl)[N:18]=[C:17]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][N+:32]=3[O-:37])[N:16]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(O)(=O)C.[CH2:42]([OH:45])[CH2:43][OH:44]>>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[C:20]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[O:28][CH3:29])=[C:19]([O:44][CH2:43][CH2:42][OH:45])[N:18]=[C:17]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][N+:32]=3[O-:37])[N:16]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 174Ethylene GlycolHCID 176Acetic AcidHCID 19595061HCID 19595061, compound

Product 1

HCID 19595072HCID 19595072, compound

Conditions

Temperature
80 °C

Procedure

216 mg of 2-[4-(4-tert-butyl-phenylsulphonylamino)-6-chloro-5-(2-methoxy-phenoxy)-pyrimidin-2-yl]-pyridine 1-oxide were added to a solution of 46 mg of Na in pure ethylene glycol and the solution which slowly resulted was heated at 80° C. overnight. The solution was poured into aqueous acetic acid, the precipitate was extracted with ethyl acetate, triturated with ether and filtered off under suction. There was obtained 2-[4-(4-tert-butyl-phenylsulphonylamino)-6-(2-hydroxy-ethoxy)-5-(2-methoxy-phenoxy)-pyrimidin-2-yl]-pyridine 1-oxide as an amorphous mass which was dried in a high vacuum at 40° C. MS: (M+H)+ =567.4.

Workup

  1. customthe solution which slowly resulted
  2. extractionthe precipitate was extracted with ethyl acetate
  3. customtriturated with ether
  4. filtrationfiltered off under suction

Sources & evidence

ORD record
ord-e90afd78654c431da407264c463e32ba
Source dataset
uspto-grants-1994_03
Patent number
US05292740

Reaction notes

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