4-Isopropylbenzyl chloride → HCID 68570748, compound

HRID 18790

Reaction equation

HRID 18790 reaction equation
[C:1]1([C@H:7]2[C@@H:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[NH:10][C:9](=[S:18])[NH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:19]([C:22]1[CH:29]=[CH:28][C:25]([CH2:26][Cl:27])=[CH:24][CH:23]=1)([CH3:21])[CH3:20]>CCO>[ClH:27].[CH:19]([C:22]1[CH:29]=[CH:28][C:25]([CH2:26][S:18][C:9]2[NH:8][C@H:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C@H:11]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:10]=2)=[CH:24][CH:23]=1)([CH3:21])[CH3:20]

Participants

4

Reactant 2

HCID 749164-Isopropylbenzyl chlorideHCID 45258634cis-4,5-Diphenylimidazolidine-2-thione

Product 1

HCID 68570748HCID 68570748, compoundYield 74.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of intermediate 25 (200 mg, 0.786 mmol) and 4-isopropylbenzyl chloride (264 mg, 1.57 mmol) in abs. EtOH (2 mL) is heated at 95° C. for 24 h. The reaction mixture is cooled to RT, evaporated to dryness, and the residue suspended in Et2O. The insoluble material is filtered to give 249 mg of the product 239. 1H NMR (DMSO-d6) δ 11.24 (s, 2 H), 7.52 (d, 2 H), 7.32 (d, 2 H), 7.20-6.90 (m, 6 H), 6.90-6.70 (m, 4 H), 5.77 (s, 2 H), 4.78 (s, 2 H), 3.02-3.85 (m, 1 H), 1.22 (d, 6 H); MS: m/z 387 (M++1).

Workup

  1. customevaporated to dryness
  2. filtrationThe insoluble material is filtered

Sources & evidence

ORD record
ord-c9b54cf78e784f52afc814d799ea151a
Source dataset
uspto-grants-2010_06
Patent number
US07741493B2

Linked notes

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