2-Nitrobenzoyl chloride → HCID 66631376, compound

HRID 1797931Notes

Reaction equation

HRID 1797931 reaction equation
[N:1]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[N:4]([C:10]1[N:15]=[CH:14][C:13]([NH2:16])=[CH:12][N:11]=1)[CH2:3][CH2:2]2.[N+:17]([C:20]1[CH:28]=[CH:27][CH:26]=[CH:25][C:21]=1[C:22]([Cl:24])=[O:23])([O-:19])=[O:18]>C1COCC1>[ClH:24].[N:1]12[CH2:7][CH2:6][CH:5]([CH2:8][CH2:9]1)[N:4]([C:10]1[N:15]=[CH:14][C:13]([NH:16][C:22](=[O:23])[C:21]3[CH:25]=[CH:26][CH:27]=[CH:28][C:20]=3[N+:17]([O-:19])=[O:18])=[CH:12][N:11]=1)[CH2:3][CH2:2]2

Participants

4

Reactant 2

HCID 118752-Nitrobenzoyl chlorideHCID 66630811HCID 66630811, compound

Product 1

HCID 66631376HCID 66631376, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-(1,4-diaza-bicyclo[3.2.2]non-4-yl)-pyrimidin-5-ylamine free base and THF (275 ml) was added to another mixture of 2-nitrobenzoylchloride (10 g, 53.9 mmol) during 45 minutes. The mixture was stirred at room temperature for 15 h. The crystals were filtered and washed with THF. The crystals where boiled in ethanol (100 ml, 96%) and the mixture was stored in the refrigerator for 3 hours. The crystals were filtered and washed with ethanol followed by diethylether. Yield 6.47 g (33%). LC-ESI-HRMS of [M+H]+ shows 369.169 Da. Calc. 369.167514 Da, dev. 4 ppm.

Workup

  1. filtrationThe crystals were filtered
  2. washwashed with THF
  3. waitthe mixture was stored in the refrigerator for 3 hours
  4. filtrationThe crystals were filtered
  5. washwashed with ethanol

Sources & evidence

ORD record
ord-aa992bd8476e4c3c9c1a1eb12ddca10d
Source dataset
uspto-grants-2013_01
Patent number
US08343960B2

Reaction notes

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