Thiourea → 2-(6,7-dihydrobenzo[b]thiophen-4(5H)-ylidene)ethyl carbamimidothioate
Reaction equation
[CH:1]([C:3]1(O)[C:11]2[CH:10]=[CH:9][S:8][C:7]=2[CH2:6][CH2:5][CH2:4]1)=[CH2:2].[NH2:13][C:14]([NH2:16])=[S:15]>C(O)(=O)C>[C:14]([S:15][CH2:2][CH:1]=[C:3]1[C:11]2[CH:10]=[CH:9][S:8][C:7]=2[CH2:6][CH2:5][CH2:4]1)(=[NH:13])[NH2:16]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
4-Vinyl-4,5,6,7-tetrahydrobenzo[b]thiophen-4-ol (10.1 g, 56 mmol) was dissolved in acetic acid (70 mL) and thiourea (4.3 g, 56 mmol) was added in one portion. The reaction was stirred at 25° C. for 2 hours and then the majority of the acetic acid was removed in vacuo. The residue was diluted with diethyl ether to afford a white solid. This was filtered off and washed with additional ether before being dried in vacuo. The title compound was isolated as the acetate salt (13.8 g, 83%).
Workup
- customthe majority of the acetic acid was removed in vacuo
- additionThe residue was diluted with diethyl ether
- customto afford a white solid
- filtrationThis was filtered off
- washwashed with additional ether
- custombefore being dried in vacuo
Sources & evidence
- ORD record
- ord-5cf01256dfb24d55b2098c46db5d2073
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09233982B2
Reaction notes
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