Benzoyl chloride → HCID 68013273, compound

HRID 1430354Notes

Reaction equation

HRID 1430354 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:10][C:11]1([CH3:28])[CH2:16][CH:15]([OH:17])[CH2:14][C:13]([CH3:19])([CH3:18])[N:12]1[N:20]=[N:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[CH3:18][C:13]1([CH3:19])[CH2:14][CH:15]([O:17][C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:16][C:11]([CH3:10])([CH3:28])[N:12]1[N:20]=[N:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 2

HCID 7412Benzoyl chlorideHCID 66718671HCID 66718671, compound

Product 1

HCID 68013273HCID 68013273, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Conditions

Temperature
23 °C

Procedure

2.15 ml Benzoylchloride are dropwise added to a solution of 4.42 g 2,2,6,6-tetramethyl-1-phenyldiazenyl-piperidin-4-ol (see example 1) and 0.1 g 4-dimethylaminopyridine in 35 ml pyridine. The resulting mixture is stirred 4 hours at 23° C., then diluted with 300 ml ice-water. The precipitate is filtered off and recrystallized twice from methanol to afford 4.43 g of benzoic acid 2,2,6,6-tetramethyl-1-phenyldiazenyl-piperidin-4-yl ester as an off-white solid, m.p. 89-91° C.

Workup

  1. filtrationThe precipitate is filtered off
  2. customrecrystallized twice from methanol

Sources & evidence

ORD record
ord-26f2452ffe564e1996a02dce91076a05
Source dataset
uspto-grants-2015_01
Patent number
US08940806B2

Reaction notes

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