5-Isothiocyanatobicyclo[2.2.1]hept-2-ene → 4-(Bicyclo[2.2.1]hept-5-en-2-yl)-1-(2-methylthiazole-5-carbonyl)thiosemicarbazide
Reaction equation
[CH:1]12[CH2:7][CH:4]([CH:5]=[CH:6]1)[CH2:3][CH:2]2[N:8]=[C:9]=[S:10].[CH3:11][C:12]1[S:13][C:14]([C:17]([NH:19][NH2:20])=[O:18])=[CH:15][N:16]=1>>[CH:1]12[CH2:7][CH:4]([CH:5]=[CH:6]1)[CH2:3][CH:2]2[NH:8][C:9](=[S:10])[NH:20][NH:19][C:17]([C:14]1[S:13][C:12]([CH3:11])=[N:16][CH:15]=1)=[O:18]Participants
3
Procedure
The title compound was prepared from a mixture of bicyclo[2.2.1]hept-5-en-2-ylisothiocyanate (50 mg, 0.33 mmol) and 2-methylthiazole-5-carboxylic acid hydrazide (58 mg, 0.36 mmol) similar to Example 80 and isolated as a white solid (10 mg, 9%). 1H NMR (DMSO-d6): 10.11 (s, 1H), 9.34 (s, 1H), 8.22 (s, 1H), 7.73 (s, 1H), 6.07 (ddd, J=8.1, 5.1, 2.7 Hz, 2H), 3.99 (s, 1H), 2.82 (brs, J=8.8 Hz, 2H), 2.72 (s, 3H), 1.52-1.35 (m, 4H).
Sources & evidence
- ORD record
- ord-dbe877e373704542a0d9adbf7a915090
- Source dataset
- uspto-grants-2004_09
- Patent number
- US06794400B2
Reaction notes
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