Diethyl Ether → HCID 10973591, compound

HRID 1824591Notes

Reaction equation

HRID 1824591 reaction equation
[Cl:1][C:2]1[C:7]([N:8]([CH3:10])[CH3:9])=[CH:6][C:5]([S:11][C:12]2[CH:22]=[CH:21][CH:20]=[CH:19][C:13]=2[C:14]([N:16]([CH3:18])[CH3:17])=[O:15])=[C:4]([N+:23]([O-:25])=[O:24])[CH:3]=1.[F:26][C:27]([F:34])([F:33])[S:28]([O:31]C)(=[O:30])=[O:29].[CH2:35](OCC)C>C(Cl)Cl>[F:26][C:27]([F:34])([F:33])[S:28]([O-:31])(=[O:30])=[O:29].[Cl:1][C:2]1[CH:3]=[C:4]([N+:23]([O-:25])=[O:24])[C:5]([S:11][C:12]2[CH:22]=[CH:21][CH:20]=[CH:19][C:13]=2[C:14]([N:16]([CH3:18])[CH3:17])=[O:15])=[CH:6][C:7]=1[N+:8]([CH3:35])([CH3:10])[CH3:9]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 9526Methyl triflateHCID 10981772HCID 10981772, compound

Product 1

HCID 10973591HCID 10973591, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(4-Chloro-5-dimethylamino-2-nitro-phenylsulfanyl)-N,N-dimethyl-benzamide (22) (0.5 g, 1.32 mmol) and methyl trifluoromethanesulfonate (0.3 g, 1.83 mmol) was heated to reflux in 5 mL of methylene chloride for 72 h. After cooled down, ethyl ether was added to the mixture. Precipitate was collected and recrystalized from CH2Cl2/ethylether repeatedly. Highly hygroscopic pale yellow powder was dried in vacuo and used directly for F-18 radiolabeling without further purifications (Yellow powder. 0.31 g, 40%): IR (cm−, neat) 3060, 1623, 1553, 1519, 1256, 1154, 1027, 784, 640; 1H NMR (200 MHz CDCl3) δ 8.53 (s, 1H), 7.74–7.90 (m, 4H), 7.69 (s, 1H), 3.69 (s, 9H), 3.40 (s, 3H), 3.06 (s, 3H); HRMS calcd for C18H2135ClN3O3S (M+) 394.0992, found 394.0999.

Workup

  1. temperatureAfter cooled down
  2. customPrecipitate was collected
  3. customrecrystalized from CH2Cl2/ethylether repeatedly
  4. customHighly hygroscopic pale yellow powder was dried in vacuo

Sources & evidence

ORD record
ord-82395f0702ab42178b796ca8f267caf5
Source dataset
uspto-grants-2006_05
Patent number
US07041851B2

Reaction notes

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