Water → 6-chloro-3-chloromethyl-3H-oxazolo[4,5-b]pyridin-2-one

HRID 258572Notes

Reaction equation

HRID 258572 reaction equation
S(Cl)([Cl:3])=O.O[CH2:6][N:7]1[C:11]2=[N:12][CH:13]=[C:14]([Cl:16])[CH:15]=[C:10]2[O:9][C:8]1=[O:17].C1(C)C=CC=CC=1.O>CCCCCC>[Cl:3][CH2:6][N:7]1[C:11]2=[N:12][CH:13]=[C:14]([Cl:16])[CH:15]=[C:10]2[O:9][C:8]1=[O:17]

Participants

6

Reactant 4

HCID 962WaterHCID 1140Toluene2×HCID 24386Thionyl ChlorideHCID 214260726-Chloro-3-(hydroxymethyl)oxazolo(4,5-b)pyridin-2(3H)-one

Product 1

HCID 214260736-chloro-3-chloromethyl-3H-oxazolo[4,5-b]pyridin-2-oneYield 83%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

39 Parts of thionyl chloride are added dropwise, in a manner ensuring that the internal temperature does not exceed 50° C., to a solution of 45 parts of 3-hydroxymethyl-6-chloro-oxazolo[4,5-b]pyridin-2-(3H)-one in 200 parts of toluene; and the whole is stirred for a further 4 hours at 40°-50° C. The resulting solution is subsequently freed from gases in a water-jet vacuum, and sufficient toluene is evaporated off to leave a crystal sludge that can still just be stirred. After the addition of 100 parts of hexane, filtration is carried out and the filter cake is washed twice with cold hexane. There are obtained 40 parts of 3-chloromethyl-6-chloro-oxazolo[4,5-b]pyridin-2-(3H)-one (83% of theory), m.p. 105°-107° C.

Workup

  1. customis evaporated off
  2. customto leave a crystal sludge that
  3. stirringcan still just be stirred
  4. washthe filter cake is washed twice with cold hexane

Sources & evidence

ORD record
ord-4d64fe1590b54ba38d13df0e6a65285e
Source dataset
uspto-grants-1977_07
Patent number
US04033975

Reaction notes

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