Thiophosgene → 5-Chloro-2-morpholinophenyl isothiocyanate

HRID 1492279Notes

Reaction equation

HRID 1492279 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1.[C:15](Cl)(Cl)=[S:16]>O1CCOCC1.O>[Cl:8][C:6]1[CH:5]=[CH:4][C:3]([N:9]2[CH2:10][CH2:11][O:12][CH2:13][CH2:14]2)=[C:2]([N:1]=[C:15]=[S:16])[CH:7]=1

Participants

5

Reactant 2

HCID 10040ThiophosgeneHCID 8461895-Chloro-2-(morpholin-4-yl)aniline

Product 1

HCID 189520985-Chloro-2-morpholinophenyl isothiocyanate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Reaction of 4-(2-amino-4-chlorophenyl)morpholine (8.5 g) with thiophosgene (4.6 ml) in dioxan (25 ml) and water (100 ml) for 30 minutes at 0° C. and for 3 hours at room temperature gave 5-chloro-2-morpholinophenyl isothiocyanate as a pale yellow solid (m.p. 86°-87° C.).

Sources & evidence

ORD record
ord-9bd12e691fb1486f8dce6eae5b0f9dea
Source dataset
uspto-grants-1994_12
Patent number
US05373008

Reaction notes

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