Thiophosgene → 5-Cyano-2-morpholinophenyl isothiocyanate

HRID 1492270Notes

Reaction equation

HRID 1492270 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[C:7]([CH:9]=1)[NH2:8])#[N:2].[C:16](Cl)(Cl)=[S:17]>O1CCOCC1.O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[C:7]([N:8]=[C:16]=[S:17])[CH:9]=1)#[N:2]

Participants

5

Reactant 2

HCID 10040ThiophosgeneHCID 189522703-Amino-4-(morpholin-4-yl)benzonitrile

Product 1

HCID 189521945-Cyano-2-morpholinophenyl isothiocyanate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Reaction of 5-cyano-2-morpholinoaniline (2 g) with thiophosgene (1.15 ml) in dioxan (2 ml) and water (25 ml) at 0° C. for 30 minutes and then at room temperature for 2 hours yielded a residue which was extracted with dichloromethane to give 5-cyano-2-morpholinophenyl isothiocyanate as an oil.

Workup

  1. customat room temperature for 2 hours yielded a residue which
  2. extractionwas extracted with dichloromethane

Sources & evidence

ORD record
ord-c77904a4b98f4428ba8ffb88f9bdc51b
Source dataset
uspto-grants-1994_12
Patent number
US05373008

Reaction notes

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