4-Aminophenol → HCID 22641092, compound

HRID 2415238Notes

Reaction equation

HRID 2415238 reaction equation
[CH3:1][C:2]1([CH3:26])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([Se:14][C:15]#[C:16][C:17]3[CH:25]=[CH:24][C:20]([C:21]([OH:23])=O)=[CH:19][CH:18]=3)[CH:5]=[CH:4][C:3]1=2.CN(C)CCCN=C=NCC.[NH2:38][C:39]1[CH:44]=[CH:43][C:42]([OH:45])=[CH:41][CH:40]=1.O>C1COCC1.C(OCC)(=O)C>[OH:45][C:42]1[CH:43]=[CH:44][C:39]([NH:38][C:21](=[O:23])[C:20]2[CH:19]=[CH:18][C:17]([C:16]#[C:15][Se:14][C:6]3[CH:5]=[CH:4][C:3]4[C:2]([CH3:1])([CH3:26])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]=4[CH:7]=3)=[CH:25][CH:24]=2)=[CH:40][CH:41]=1

Participants

7

Reactant 4

HCID 4034-AminophenolHCID 962WaterHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 10787760HCID 10787760, compound

Product 1

HCID 22641092HCID 22641092, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 250 mg (0.63 mmol) of 4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthylselanylethynyl)benzoic acid obtained in Example 5, 169 mg (1.25 mmol) of 1-hydroxybenzoctriazole, 240 mg (1.25 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (EDC) and 82 mg (0.75 mmol) of 4-aminophenol in 20 ml of THF is stirred at room temperature for 15 h. Water and ethyl acetate are then added. After stirring and separation of the phases by settling, the aqueous phase is extracted with ethyl acetate. The organic phases are then combined and washed with water, dried over magnesium sulphate and concentrated on a rotary evaporator under vacuum at 40° C. The product is purified on a column of silica (ethyl acetate 20/heptane 80). 200 mg (65%) of a white solid are obtained. m.p.=202° C.

Workup

  1. customseparation of the phases
  2. extractionthe aqueous phase is extracted with ethyl acetate
  3. washwashed with water
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated on a rotary evaporator under vacuum at 40° C
  6. customThe product is purified on a column of silica (ethyl acetate 20/heptane 80)

Sources & evidence

ORD record
ord-9f0fbe7b9fda432e91ec8ce463cd3990
Source dataset
uspto-grants-2004_11
Patent number
US06818666B2

Reaction notes

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