Thionyl Chloride → HCID 20557444, compound

HRID 1660115Notes

Reaction equation

HRID 1660115 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[NH:4][C:3](=O)[C:2]1=[O:12].S(Cl)([Cl:15])=O>C1(C)C=CC=CC=1.CN(C)C=O>[Cl:15][CH:3]1[NH:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[O:1][C:2]1=[O:12]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 771482H-1,4-Benzoxazine-2,3(4H)-dione

Product 1

HCID 20557444HCID 20557444, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 25 g of 4H-1,4-benzoxazin-2,3-dione and 14.3 ml of thionylchloride in 500 ml of toluene and 5 ml dimethylformamide was heated at about 130° C. until all solids dissolved (about 2-3 hours). The solution was decanted hot (if the solution was deeply colored, charcoal was added and following stirring, the solution was filtered) and the organic solution was evaporated to dryness to give 29 g of 3-chloro-4H-1,4-benzoxazin-2-one, m.p. 133°-136° C.

Workup

  1. dissolutiondissolved (about 2-3 hours)
  2. customThe solution was decanted hot (if the solution
  3. additioncharcoal was added
  4. filtrationthe solution was filtered) and the organic solution
  5. customwas evaporated to dryness

Sources & evidence

ORD record
ord-040a71810e0a4e05b143f21c4d41d150
Source dataset
uspto-grants-1981_12
Patent number
US04307091

Reaction notes

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