1-Chloromethyl-2-methylnaphthalene → HCID 68571179, compound

HRID 18777Notes

Reaction equation

HRID 18777 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.[Cl:19][CH2:20][C:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23][C:22]=1[CH3:31]>CCO>[ClH:19].[CH3:31][C:22]1[CH:23]=[CH:24][C:25]2[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:21]=1[CH2:20][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 811061-Chloromethyl-2-methylnaphthaleneHCID 45258634cis-4,5-Diphenylimidazolidine-2-thione

Product 1

HCID 68571179HCID 68571179, compoundYield 65.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of intermediate 25 (200 mg, 0.786 mmol) and 1-chloromethyl-2-methyl-naphthalene (299 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 229 mg of the product 226. 1H NMR (DMSO-d6) δ 11.40 (s, 2 H), 8.36 (d, 1 H), 8.10-7.80 (m, 2 H), 7.80-7.30 (m, 3 H), 7.30-6.75 (m, 10 H), 5.90 (s, 2 H), 5.30 (s, 2 H), 2.62 (s, 3 H); MS: m/z 409 (M++1).

Workup

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

Sources & evidence

ORD record
ord-649d97d8f8864912961228516f84466d
Source dataset
uspto-grants-2010_06
Patent number
US07741493B2

Reaction notes

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