4-Toluenesulfonyl chloride → HCID 178427378, compound

HRID 1577154Notes

Reaction equation

HRID 1577154 reaction equation
[C:1]1([N:7]=[C:8]2[NH:12][CH2:11][CH2:10][NH:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Li])CCC.[C:18]1([CH3:28])[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1>C1COCC1.CCCCCC>[S:24]([N:12]1[CH2:11][CH2:10][NH:9][C:8]1=[N:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)([C:21]1[CH:22]=[CH:23][C:18]([CH3:28])=[CH:19][CH:20]=1)(=[O:26])=[O:25]

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 178418339ButyllithiumHCID 178420483HCID 178420483, compound

Product 1

HCID 178427378HCID 178427378, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

2-(Phenylimino)imidazolidine (0.773 g, 4.8 mmoles) is dissolved in dry THF (15 ml), cooled to -78° C. under nitrogen protected from moisture and 2.4 N butyllithium in hexane (2.0 ml) is added. Then p-toluenesulfonyl chloride (0.953 g, 5 mmoles) in THF (3 ml) at -78° C. is added. The mixture is stirred for 90 minutes and allowed to warm to ambient temperature. The volatiles are evaporated in vacuo and water and ether are added. Crystals separate in the ether layer which are filtered and recrystallized from isopropanol to remove some bistosyl derivative. The major product, confirmed by n.m.r is N'-Tosyl-2-(phenylimino)imidazolidine, (610 mg, 40%), m.p. 174°-177° C.

Workup

  1. additionis added
  2. temperatureto warm to ambient temperature
  3. customThe volatiles are evaporated in vacuo and water and ether
  4. additionare added
  5. customCrystals separate in the ether layer which
  6. filtrationare filtered
  7. customrecrystallized from isopropanol
  8. customto remove some bistosyl derivative

Sources & evidence

ORD record
ord-76cb4ed7da7f405cadea6baba8ebe819
Source dataset
uspto-grants-1981_09
Patent number
US04287201

Reaction notes

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