Ethylamine → HCID 15961201, compound
Reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[O:9][C:8]([CH2:10][S:11][CH2:12][CH2:13][NH2:14])=[CH:7][CH:6]=1)[CH3:3].CO[C:17]1[C:21](OC)=[N:20][S:19](=[O:24])[N:18]=1.[CH2:25]([NH2:27])[CH3:26]>CO>[CH3:3][N:2]([CH2:4][C:5]1[O:9][C:8]([CH2:10][S:11][CH2:12][CH2:13][NH:14][C:17]2[C:21]([NH:27][CH2:25][CH3:26])=[N:20][S:19](=[O:24])[N:18]=2)=[CH:7][CH:6]=1)[CH3:1]Participants
Procedure
A solution of 2-[(5-dimethylaminomethyl-2-furyl)methylthio]ethylamine (2.64 g; 12.3 mmoles) in 25 ml of dry methanol was added dropwise over a period of 30 minutes to a well stirred solution of 3,4-dimethoxy-1,2,5-thiadiazole 1-oxide (2.0 g; 12.3 mmoles) in 75 ml of dry methanol that had been cooled to 8° in an ice-water bath. After 15 minutes, 4.0 ml of ethylamine was added and the mixture stirred at ambient temperature for 1 hour. The reaction mixture was evaporated under reduced pressure and the residue placed on 55 g of silica gel and chromatographed using a gradient elution of methylene chloride-methanol. The appropriate fractions were combined, evaporated under reduced pressure and the residue treated with ether and decanted. The residue was treated with fresh ether to give 1.5 g of the title compound, mp 68°-74°.
Workup
- temperaturehad been cooled to 8° in an ice-water bath
- customThe reaction mixture was evaporated under reduced pressure
- customchromatographed
- washa gradient elution of methylene chloride-methanol
- customevaporated under reduced pressure
- additionthe residue treated with ether
- customdecanted
- additionThe residue was treated with fresh ether
Sources & evidence
- ORD record
- ord-45a1ca0b547c4bbe97c26493f73effb8
- Source dataset
- uspto-grants-1983_02
- Patent number
- US04374248
Reaction notes
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