2-Chloroethyl Isothiocyanate → HCID 68725836, compound

HRID 1510336Notes

Reaction equation

HRID 1510336 reaction equation
[NH2:1][CH:2]([C:12]1[C:20]2[O:19][C:18]([F:22])([F:21])[O:17][C:16]=2[CH:15]=[CH:14][CH:13]=1)[CH2:3][C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[C:6]([CH3:11])[CH:5]=1.Cl[CH2:24][CH2:25][N:26]=[C:27]=[S:28]>C(OCC)C>[S:28]1[CH2:24][CH2:25][N:26]=[C:27]1[N:26]1[CH2:25][CH2:24][S:28][C:27]1=[N:1][CH:2]([C:12]1[C:20]2[O:19][C:18]([F:22])([F:21])[O:17][C:16]=2[CH:15]=[CH:14][CH:13]=1)[CH2:3][C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[C:6]([CH3:11])[CH:5]=1

Participants

4

Reactant 2

HCID 1386612-Chloroethyl IsothiocyanateHCID 68723348HCID 68723348, compound

Product 1

HCID 68725836HCID 68725836, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 1-amino-1-(2,2-difluoro-benzo[1,3]dioxol-4-yl)-2-(3,5-dimethylphenyl)-ethane (0.39 g) in diethyl ether was treated at 0° C. with 2-chloroethyl isothiocyanate (0.16 g) and stirring was continued for 5 h at this temperature. The mixture was quenched with an aqueous sodium hydroxide solution (1 M, 4 ml) and water (15 ml) and stirred for 15 minutes. The organic phase was washed with water, the aqueous phase was extracted with diethyl ether, the combined organic phases were dried over sodium sulphate and the solvent was removed in vacuo. The remainder was purified by column chromatography to yield 0.1 g of the title compound.

Workup

  1. customThe mixture was quenched with an aqueous sodium hydroxide solution (1 M, 4 ml) and water (15 ml)
  2. stirringstirred for 15 minutes
  3. washThe organic phase was washed with water
  4. extractionthe aqueous phase was extracted with diethyl ether
  5. dry with materialthe combined organic phases were dried over sodium sulphate
  6. customthe solvent was removed in vacuo
  7. customThe remainder was purified by column chromatography

Sources & evidence

ORD record
ord-6965589866564a4f98cc5f1cd73c54e4
Source dataset
uspto-grants-2012_07
Patent number
US08211924B2

Reaction notes

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