2-(Trifluoromethoxy)benzyl chloride → HCID 68569655, compound

HRID 2053560Notes

Reaction equation

HRID 2053560 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.[F:19][C:20]([F:31])([F:30])[O:21][C:22]1[CH:29]=[CH:28][CH:27]=[CH:26][C:23]=1[CH2:24][Cl:25]>CCO>[ClH:25].[F:19][C:20]([F:30])([F:31])[O:21][C:22]1[CH:29]=[CH:28][CH:27]=[CH:26][C:23]=1[CH2:24][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 46566772-(Trifluoromethoxy)benzyl chlorideHCID 45258634cis-4,5-Diphenylimidazolidine-2-thione

Product 1

HCID 68569655HCID 68569655, compoundYield 55.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of intermediate 25 (200 mg, 0.786 mmol) and 2-trifluoromethoxybenzyl chloride (0.331 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 202 mg of the product 215. 1H NMR (DMSO-d6) δ 11.32 (s, 2H), 7.85 (d, 1H), 7.70-7.40 (m, 3H), 7.20-6.70 (m, 10H), 5.80 (s, 2H), 4.85 (s, 2H); MS: m/z 429 (M++1).

Workup

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

Sources & evidence

ORD record
ord-b42ae3e1862d4518a562f6670b3c1657
Source dataset
uspto-grants-2008_02
Patent number
US07326792B2

Reaction notes

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