Triethylamine → 1-Ethyl-3-(4,5,6,7-tetrahydrobenzo[b]thien-4-yl)thiourea
Reaction equation
Cl.[S:2]1[CH:6]=[CH:5][C:4]2[CH:7]([NH2:11])[CH2:8][CH2:9][CH2:10][C:3]1=2.C(N(CC)CC)C.[CH2:19]([N:21]=[C:22]=[S:23])[CH3:20]>O1CCCC1>[CH2:19]([NH:21][C:22]([NH:11][CH:7]1[C:4]2[CH:5]=[CH:6][S:2][C:3]=2[CH2:10][CH2:9][CH2:8]1)=[S:23])[CH3:20]Participants
Conditions
- Temperature
- 50 °C
Procedure
A sample of 9.48 grams of 4,5,6,7-tetrahydrobenzo[b]thiophen-4-amine hydrochloride is stirred in 100 ml. of dry tetrahydrofuran, and 6.06 grams of triethylamine is added. After stirring for 15 to 30 minutes, 5.23 grams of ethyl isothiocyanate in 20 ml. of dry tetrahydrofuran is added dropwise, and the mixture is heated for 2 hours at 50° C. The mixture is cooled and filtered, and the filter cake is washed with hexane. The filtrate is evaporated to dryness and poured on ice. The oil is extracted with ether, and the extract is washed with 1 N sulfuric acid, water, and saturated sodium bicarbonate solution. The ether extract is dried and evaporated to dryness to afford an oil. This oil crystallizes in ether to afford 1-ethyl-3-(4,5,6,7-tetrahydrobenzo[b]thien-4-yl)thiourea, melting point 106° C. to 112° C.
Workup
- temperatureThe mixture is cooled
- filtrationfiltered
- washthe filter cake is washed with hexane
- customThe filtrate is evaporated to dryness
- additionpoured on ice
- extractionThe oil is extracted with ether
- washthe extract is washed with 1 N sulfuric acid, water, and saturated sodium bicarbonate solution
- extractionThe ether extract
- customis dried
- customevaporated to dryness
- customto afford an oil
- customThis oil crystallizes in ether
Sources & evidence
- ORD record
- ord-a1393d7a6d0c4b0296b8018979af8bb3
- Source dataset
- uspto-grants-1980_03
- Patent number
- US04191830
Reaction notes
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