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Lithium amide → 2,2,6,6-Tetramethylpiperidin-4-yl 3-(5-Phenylsulfonylbenzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydrocinnamate

HRID 28327
Notes
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Reaction equation

HRID 28327 reaction equation
[C:1]1([S:7]([C:10]2[CH:35]=[CH:34][C:13]3=[N:14][N:15]([C:17]4[CH:18]=[C:19]([CH:26]=[C:27]([C:30]([CH3:33])([CH3:32])[CH3:31])[C:28]=4[OH:29])[CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])[N:16]=[C:12]3[CH:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:36][C:37]1([CH3:46])[CH2:42]C(O)[CH2:40][C:39]([CH3:45])([CH3:44])[NH:38]1.[NH2-].[Li+]>>[C:1]1([S:7]([C:10]2[CH:35]=[CH:34][C:13]3=[N:14][N:15]([C:17]4[CH:18]=[C:19]([CH:26]=[C:27]([C:30]([CH3:32])([CH3:31])[CH3:33])[C:28]=4[OH:29])[CH2:20][CH2:21][C:22]([O:24][CH:25]4[CH2:40][C:39]([CH3:45])([CH3:44])[NH:38][C:37]([CH3:46])([CH3:42])[CH2:36]4)=[O:23])[N:16]=[C:12]3[CH:11]=2)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 3

HCID 24532Lithium amideHCID 754714-Hydroxy-2,2,6,6-tetramethylpiperidineHCID 22595036Methyl 3-(5-phenylsulfonylbenzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydrocinnamate

Product 1

HCID 103045142,2,6,6-Tetramethylpiperidin-4-yl 3-(5-Phenylsulfonylbenzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydrocinnamateYield 103.4%

Conditions

Temperature
50 °C

Procedure

Methyl 3-(5-phenylsulfonylbenzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydrocinnamate (10 g, 0.02 mol), xylenes (100 g, 0.93 mol) and 2,2,6,6-tetramethyl-4-hydroxypiperidine (4.0 g, 0.025 mol) are charged to a reactor. The contents are heated to reflux in order to dry the xylenes. The contents are cooled to 50° C. at which time lithium amide (0.4 g, 0.017 mol) is added. The reaction mass is then heated to reflux and held at that temperature for 3.5 hours. The reaction is monitored by thin layer chromatography. The reaction mass is cooled to 50° C. and washed thrice with 100 g of water. The xylene is removed by distillation under vacuum to give 12.8 g of an orange oil which is subjected to silica gel chromatography for purification using ethyl acetate as the eluent. The title compound is obtained in a yield of 9.6 g (77%) as a yellow semi-solid, melting at 85-125° C., whole structure is confirmed by mass spectrometry and 1Hnmr.

Workup

  1. temperatureThe contents are heated
  2. temperatureto reflux in order
  3. dry with materialto dry the xylenes
  4. additionis added
  5. temperatureThe reaction mass is then heated
  6. temperatureto reflux
  7. washwashed thrice with 100 g of water
  8. customThe xylene is removed by distillation under vacuum

Sources & evidence

ORD record
ord-cbc1b0bfceec476489d405c32b68d102
Source dataset
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07419513B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes