1,2,3-Thiadiazole-4-carbaldehyde → 4-(Bicyclo[2.2.1]hept-5-en-2-yl)-1-(1,2,3-thiadiazol-4-ylmethylidene)thiosemicarbazide

HRID 1007280Notes

Reaction equation

HRID 1007280 reaction equation
[CH:1]12[CH2:7][CH:4]([CH:5]=[CH:6]1)[CH2:3][CH:2]2[NH:8][C:9]([NH:11][NH2:12])=[S:10].[S:13]1[CH:17]=[C:16]([CH:18]=O)[N:15]=[N:14]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:11][N:12]=[CH:18][C:16]1[N:15]=[N:14][S:13][CH:17]=1

Participants

3

Reactant 2

HCID 27372711,2,3-Thiadiazole-4-carbaldehydeHCID 2740681N1-bicyclo[2.2.1]hept-5-en-2-ylhydrazine-1-carbothioamide

Product 1

HCID 850590584-(Bicyclo[2.2.1]hept-5-en-2-yl)-1-(1,2,3-thiadiazol-4-ylmethylidene)thiosemicarbazide

Procedure

The title compound was prepared from a mixture of N1-bicyclo[2.2.1]hept-5-en-2-ylhydrazine-1-carbothioamide (35 mg, 0.21 mmol) and 1,2,3-thiadiazole-4-carboxaldehyde (33mg, 0.287 mmol) similar to Example 3 and isolated as a white solid (47 mg, 80%). 1H NMR (CDCl3): 9.95 (s, 1H), 8.85 (s, 1H), 7.70 (brs, 1H), 6.16 (ddd, J=8.1, 5.1, 2.7 Hz, 2H), 4.27 (t, J=8.7 Hz, 1H), 3.06 (s, 1H), 2.96 (s, 1H), 1.92 (ddd, J=7.6, 7.0, 2.4 Hz, 1H), 1.67 (m, 1H), 1.51-1.40 (m, 2H).

Sources & evidence

ORD record
ord-e7d3f468497046b18863b0a80547dc2d
Source dataset
uspto-grants-2004_09
Patent number
US06794400B2

Reaction notes

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