Iodoethane → HCID 13424103, compound

HRID 1980497Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1([CH2:14][N:15]2[CH:19]=[N:18][CH:17]=[N:16]2)[NH:13][CH2:12][CH2:11][S:10]1.[CH3:20][CH2:21]CCCC.C([Li])CCC.C(I)C>O1CCCC1>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1([CH2:14][N:15]2[CH:19]=[N:18][CH:17]=[N:16]2)[N:13]([CH2:20][CH3:21])[CH2:12][CH2:11][S:10]1

Participants

Conditions

Temperature: -50 °C

Procedure

2.0 g of 2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazole-1-yl methyl) thiazolidine used in Working Example 7 was dissolved in anhydrous tetrahydrofuran. After cooling the solution to -50° C., 4.5 ml of a n-hexane solution containing 15% of n-butyl lithium was added and the mixture was stirred for 30 minutes at the same temperature. Then, 2.2 g of ethyl iodide was added and the mixture was reacted for 1 hour at the same temperature. Then, the temperature was gradually raised to room temperature. After distilling off tetrahydrofuran under reduced pressure, the reaction product was purified by silica gel column chromatography using a solvent mixture of chloroform and ethyl acetate as the developer, whereby 1.0 g of 2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazole-1-yl methyl)-3-ethyl thiazolidine (Compound No. 56 in Table 1) was obtained.

Workup

additionwas added
customthe mixture was reacted for 1 hour at the same temperature
temperatureThen, the temperature was gradually raised to room temperature
distillationAfter distilling off tetrahydrofuran under reduced pressure
customthe reaction product was purified by silica gel column chromatography
additiona solvent mixture of chloroform and ethyl acetate as the developer

Sources & evidence

ORD record: ord-71575991f03c4bce8f748e93a7cdb7ee
Source dataset: uspto-grants-1985_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04510154

Reaction notes

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