Lawesson's reagent → N-[4-chloro-3-[(4-morpholinylimino)methyl]phenyl]-2-methyl-3-furancarbothioamide

HRID 1416552Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[CH:15]=[CH:14][O:13][C:12]=2[CH3:16])=O)=[CH:4][C:3]=1[CH:17]=[N:18][N:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1.C(=O)(O)[O-].[Na+].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:39])=CC=1.[O-2].[Al+3].[O-2].[O-2].[Al+3]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[CH:15]=[CH:14][O:13][C:12]=2[CH3:16])=[S:39])=[CH:4][C:3]=1[CH:17]=[N:18][N:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1

Participants

Conditions

Temperature: 85 °C

Procedure

A reaction mixture of N-[4-chloro-3-[(4-morpholinylimino)methyl]phenyl]-2-methyl-3-furancarboxamide (1.0 g), sodium bicarbonate (2.5 g), Lawesson's reagent (1.2 g) in toluene (25 ml) was heated at 85° C. for 4 hours. After cooling, the reaction mixture was passed through a plug of aluminum oxide, followed by elution with ether. Evaporation of the eluant gave 0.5 g of N-[4-chloro-3-[(4-morpholinylimino)methyl]phenyl]-2-methyl-3-furancarbothioamide as a yellow solid, mp 142-143° C.

Workup

temperatureAfter cooling
washfollowed by elution with ether
customEvaporation of the eluant

Sources & evidence

ORD record: ord-455cfd4650004561aa01a7e9062e227f
Source dataset: uspto-grants-1999_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05914351

Reaction notes

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