Thiophosgene → HCID 18952176, compound

HRID 1492283Notes

Reaction equation

HRID 1492283 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)=[C:6]([CH:8]=1)[NH2:7].[C:15](Cl)(Cl)=[S:16]>O1CCOCC1.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:9]2[CH2:10][CH2:11][O:12][CH2:13][CH2:14]2)=[C:6]([N:7]=[C:15]=[S:16])[CH:8]=1

Participants

5

Reactant 2

HCID 10040ThiophosgeneHCID 6485404AKOS B022015

Product 1

HCID 18952176HCID 18952176, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 5-fluoro-2-morpholino aniline (6 g) and thiophosgene (5.2 g) in dioxan (20 ml) and water (40 ml) was stirred at 0° C. for 15 minutes and at room temperature for one hour to yield a residue which was extracted with dichloromethane to give an oil which was purified by chromatography on a silica gel column (mesh 100-200) using a 1:9 mixture of ethylacetate and hexane as eluant to give 5-fluoro-2-morpholinophenyl isothiocyanate as an oil.

Workup

  1. customto yield a residue which
  2. extractionwas extracted with dichloromethane
  3. customto give an oil which
  4. customwas purified by chromatography on a silica gel column (mesh 100-200)
  5. additiona 1:9 mixture of ethylacetate and hexane as eluant

Sources & evidence

ORD record
ord-c01e1989473c4429b3918fce148ef1a5
Source dataset
uspto-grants-1994_12
Patent number
US05373008

Reaction notes

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