3,5-dichloro-2-amino-N-(2-hydroxyethoxy)benzamide → 3-(3,5-Dichloro-2-aminophenyl)-5,6-dihydro-1,4,2-dioxazine

HRID 558066Notes

Reaction equation

HRID 558066 reaction equation
[Cl:1][C:2]1[C:3]([NH2:16])=[C:4]([CH:12]=[C:13]([Cl:15])[CH:14]=1)[C:5]([NH:7][O:8][CH2:9][CH2:10][OH:11])=O>S(Cl)(Cl)=O>[Cl:1][C:2]1[C:3]([NH2:16])=[C:4]([C:5]2[O:11][CH2:10][CH2:9][O:8][N:7]=2)[CH:12]=[C:13]([Cl:15])[CH:14]=1

Participants

3

Reactant 1

HCID 866307723,5-dichloro-2-amino-N-(2-hydroxyethoxy)benzamide

Product 1

HCID 577311733-(3,5-Dichloro-2-aminophenyl)-5,6-dihydro-1,4,2-dioxazine

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

At 20° C., 30 ml of thionyl chloride are initially charged and 3 g of 3,5-dichloro-2-amino-N-(2-hydroxyethoxy)benzamide are added in 3 portions with stirring. The mixture is stirred at 70° C. for 12 h. The reaction mixture is then cooled and carefully poured onto ice-water. The mixture is extracted twice with in each case 150 ml of dichloromethane and the extracts are dried with sodium sulphate and evaporated to dryness using a rotary evaporator.

Workup

  1. stirringThe mixture is stirred at 70° C. for 12 h
  2. temperatureThe reaction mixture is then cooled
  3. additioncarefully poured onto ice-water
  4. extractionThe mixture is extracted twice with in each case 150 ml of dichloromethane
  5. dry with materialthe extracts are dried with sodium sulphate
  6. customevaporated to dryness
  7. customa rotary evaporator

Sources & evidence

ORD record
ord-6b4dd4e291bb4e8c9bff53d01c6a10c7
Source dataset
uspto-grants-2011_11
Patent number
US08062995B2

Reaction notes

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