N-tert-Butyl-N'-propan-2-ylthiourea → 2-t-Butylimino-3-isopropyl 5-(p-fluorophenyl)-tetrahydro-1,3,5-thiadiazin-4-one
Reaction equation
[CH:1]([NH:4][C:5]([NH:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[S:6])([CH3:3])[CH3:2].Cl[CH2:13][N:14]([C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=1)[C:15](Cl)=[O:16]>>[C:8]([N:7]=[C:5]1[N:4]([CH:1]([CH3:3])[CH3:2])[C:15](=[O:16])[N:14]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[CH2:13][S:6]1)([CH3:9])([CH3:11])[CH3:10]Participants
3
Procedure
In a similar manner, 1.7 g (0.01 mole) of 1-isopropyl-3-t-butylthiourea was reacted with 2.2 g (0.01 mole) of N-chloromethyl-N-(p-fluorophenyl)-carbamoyl chloride to obtain 2-t-butylimino-3-isopropyl 5-(p-fluorophenyl)-tetrahydro-1,3,5-thiadiazin-4-one (compound No. 282): ##STR140## in the form of hydrochloride melting at 160°-195° C. Yield 2.8 g (80%). The crystals were suspended in 20 ml of water and treated in a manner similar to that described above to obtain white crystals of the free base melting at 109°-110° C. (isopropanol). Yield 2.0 g (63%).
Sources & evidence
- ORD record
- ord-78583a659a114113a9951e3f62afa301
- Source dataset
- uspto-grants-1979_06
- Patent number
- US04159328
Reaction notes
Loading…