Ethyl 4-(Chloromethyl)benzoate → HCID 68565802, compound

HRID 18757Notes

Reaction equation

HRID 18757 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.[CH2:19]([O:21][C:22](=[O:31])[C:23]1[CH:28]=[CH:27][C:26]([CH2:29][Cl:30])=[CH:25][CH:24]=1)[CH3:20]>CCO>[ClH:30].[CH2:19]([O:21][C:22](=[O:31])[C:23]1[CH:28]=[CH:27][C:26]([CH2:29][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:25][CH:24]=1)[CH3:20]

Participants

4

Reactant 2

HCID 276519Ethyl 4-(Chloromethyl)benzoateHCID 45258634cis-4,5-Diphenylimidazolidine-2-thione

Product 1

HCID 68565802HCID 68565802, compoundYield 78.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of intermediate 25 (200 mg, 0.786 mmol) and 4-chloromethylbenzoic acid ethyl ester (0.268 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 278 mg of the product 205. 1H NMR (DMSO-d6) δ 11.20 (s, 2 H), 8.00 (d, 2 H), 7.75 (d, 2 H), 7.15-6.90 (m, 6 H), 6.90-6.65 (m, 4 H), 5.78 (s, 2 H), 4.90 (s, 2 H), 4.35 (q, 2 H), 1.32 (t, 3 H); MS: m/z 417 (M++1).

Workup

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

Sources & evidence

ORD record
ord-4ddc74b2f5e64e3f9f2aff935a0ea309
Source dataset
uspto-grants-2010_06
Patent number
US07741493B2

Reaction notes

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