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Triethylamine → 3-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]-N,N-dicyclohexylpropanamide

HRID 5493
Notes
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Reaction equation

HRID 5493 reaction equation
[CH:1]1([N:7]([CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[C:8](=[O:11])[CH:9]=[CH2:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:18][C:19]([C:22]1[CH:27]=[C:26]([SH:28])[CH:25]=[C:24]([C:29]([CH3:32])([CH3:31])[CH3:30])[C:23]=1[OH:33])([CH3:21])[CH3:20].C(N(CC)CC)C>CO>[CH3:32][C:29]([C:24]1[CH:25]=[C:26]([S:28][CH2:10][CH2:9][C:8]([N:7]([CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)=[O:11])[CH:27]=[C:22]([C:19]([CH3:21])([CH3:20])[CH3:18])[C:23]=1[OH:33])([CH3:30])[CH3:31]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 703702,6-Di-tert-butyl-4-mercaptophenolHCID 101054982-Propenamide, N,N-dicyclohexyl-

Product 1

HCID 98261403-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]-N,N-dicyclohexylpropanamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title compound of Example 3 (1.9 g, 0.008 mole), 2,6-bis(1,1-dimethylethyl)-4-mercaptophenol(2 g, 0.008 mole) and triethylamine (0.5 ml) were stirred in methanol (25 ml) for about 12 hours. The solvent was removed in vacuo on a rotary evaporator, the crude material purified by chromatography on silica and recrystallized from hexane, m.p. ca. 168.5°-172° C.

Workup

  1. customThe solvent was removed in vacuo on a rotary evaporator
  2. customthe crude material purified by chromatography on silica
  3. customrecrystallized from hexane, m.p. ca. 168.5°-172° C.

Sources & evidence

ORD record
ord-83a7fad34b684fd8a233fc5ded25c4c5
Source dataset
uspto-grants-1993_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05244899

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes