Triethylamine → HCID 9860616, compound

HRID 865638Notes

Reaction equation

[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][C:3]1=O.[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:16]=[N:17][C:18](=[O:21])[S:19][CH:20]=2)=[CH:11][CH:10]=1.C(N(CC)CC)C.Cl.ClC1C=CN=CC=1>CC(C)=O.CCOCC>[N:2]1[CH:1]=[CH:6][C:5]([NH:8][C:9]2[CH:10]=[CH:11][C:12]([C:15]3[CH2:20][S:19][C:18](=[O:21])[NH:17][N:16]=3)=[CH:13][CH:14]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a N-methyl-2-pyrrolidone solution (3 mL) containing 5-(4-aminophenyl)-2H-1,3,4-thiadiazine-2-one (0.27 g), triethylamine (90 μL) and 4-chloropyridine hydrochloride (0.20 g) were added in this order by heating at 100° C. with stirring, followed by further stirring with the temperature maintained for four hours. The reacted mixture was cooled and diluted with acetone (10 mL) and ether (15 mL). The precipitated crystal was separated by filtration, air-dried, dissolved in warm water (50 mL), and adjusted to pH8 with saturated potassium carbonate. The precipitated solid was separated by filtration, and purified by a silica gel column chromatography to obtain the captioned compound (0.26 g). Yield was 70.3%. melting point: 222° to 225° C. (decomposition)

Workup

additionwere added in this order
stirringby further stirring with the temperature
temperaturemaintained for four hours
temperatureThe reacted mixture was cooled
customThe precipitated crystal was separated by filtration
customair-dried
dissolutiondissolved in warm water (50 mL)
customThe precipitated solid was separated by filtration
custompurified by a silica gel column chromatography

Sources & evidence

ORD record: ord-a4a677e4aa92450b954942d39aca0939
Source dataset: uspto-grants-1996_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05567699

Reaction notes

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