1-(Chloromethyl)-2-iodobenzene → HCID 68569425, compound

HRID 18773

Reaction equation

HRID 18773 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.[I:19][C:20]1[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=1[CH2:22][Cl:23]>CCO>[ClH:23].[I:19][C:20]1[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=1[CH2:22][S:18][C:9]1[NH:8][C@H:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C@H:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:10]=1

Participants

4

Reactant 2

HCID 1010641-(Chloromethyl)-2-iodobenzeneHCID 45258634cis-4,5-Diphenylimidazolidine-2-thione

Product 1

HCID 68569425HCID 68569425, compoundYield 67.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of intermediate 25 (200 mg, 0.786 mmol) and 2-iodobenzyl chloride (396 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 270 mg of the product 222. 1H NMR (DMSO-d6) δ 11.43 (s, 2 H), 8.00 (d, 1 H), 7.82 (d, 1 H), 7.48 (t, 1 H), 7.30-7.00 (m, 7 H), 7.00-6.80 (m, 4 H), 5.82 (s, 2 H), 4.88 (s, 2 H); MS: m/z 471 (M++1).

Workup

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

Sources & evidence

ORD record
ord-93857ffb5d4c493396b4a90d3fb71889
Source dataset
uspto-grants-2010_06
Patent number
US07741493B2

Linked notes

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