Hydrochloric Acid → 2,2-difluoro-5-isothiocyanatobenzo[d][1,3]dioxole

HRID 854613Notes

Reaction equation

HRID 854613 reaction equation
[CH:1]1[C:6]([NH2:7])=[CH:5][C:4]2[O:8][C:9]([F:12])([F:11])[O:10][C:3]=2[CH:2]=1.Cl.[C:14](Cl)(Cl)=[S:15].ClCCl>O>[N:7]([C:6]1[CH:1]=[CH:2][C:3]2[O:10][C:9]([F:11])([F:12])[O:8][C:4]=2[CH:5]=1)=[C:14]=[S:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 10040ThiophosgeneHCID 27368935-Amino-2,2-difluoro-1,3-benzodioxole

Product 1

HCID 115647562,2-difluoro-5-isothiocyanatobenzo[d][1,3]dioxole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

34.6 g of 5-amino-2,2-difluorobenzodioxole were added dropwise to a solution of 90 ml of conc. hydrochloric acid in 350 ml of water. The mixture was stirred for a further 30 minutes and then 27 g of thiophosgene were metered in rapidly. The mixture was stirred at the given temperature for a further 3 hours, the almost colourless suspension was admixed with 150 ml of dichloromethane and the dichloromethane was removed. The crude product was distilled at 45 mbar. 28 g (=89% of theory) were obtained as a colourless to yellowish liquid.

Workup

  1. stirringThe mixture was stirred at the given temperature for a further 3 hours
  2. customthe dichloromethane was removed
  3. distillationThe crude product was distilled at 45 mbar
  4. custom28 g (=89% of theory) were obtained as a colourless to yellowish liquid

Sources & evidence

ORD record
ord-af0e0aa75d884876904d84349be22a7f
Source dataset
uspto-grants-2007_08
Patent number
US07259267B2

Reaction notes

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