p-Toluenesulfonic acid → HCID 21105481, compound

HRID 2043096Notes

Reaction equation

HRID 2043096 reaction equation
[CH2:1]([O:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=O)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].O1[C:19]2([CH2:23][CH2:22][N:21]([C:24]3[CH:29]=[CH:28][C:27]([NH2:30])=[CH:26][CH:25]=3)[CH2:20]2)[O:18]CC1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(N(CC)CC)C>CC(C)=O.O>[CH2:1]([O:5][C:6]1[CH:7]=[CH:8][C:9]([C:10]([NH:30][C:27]2[CH:28]=[CH:29][C:24]([N:21]3[CH2:22][CH2:23][C:19](=[O:18])[CH2:20]3)=[CH:25][CH:26]=2)=[O:12])=[CH:13][CH:14]=1)[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 8471TriethylamineHCID 729714-Butoxybenzoic acidHCID 211054324-(1,4-Dioxa-7-azaspiro[4,4]non-7-yl)phenylamine

Product 1

HCID 21105481HCID 21105481, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

4-Butoxybenzoic acid was reacted with 4-(1,4-dioxa-7-azaspiro[4.4]non-7-yl)phenylamine by method E. The resulting amide (0.25 g) in acetone (10 ml) was mixed with para-toluenesulfonic acid (monohydrate, 109 mg), and the mixture was refluxed for 8 hours. After addition of triethylamine (0.5 ml), the mixture was diluted with water and extracted with ethyl acetate. The organic phase was dried over magnesium sulfate and concentrated. The product with the molecular weight of 352.44 (C21H24N2O3); MS (ESI): 353 (M+H+) was obtained in this way.

Workup

  1. temperaturethe mixture was refluxed for 8 hours
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. concentrationconcentrated
  5. customMS (ESI): 353 (M+H+) was obtained in this way

Sources & evidence

ORD record
ord-3c4bb91f59244840b1cea6c75ac5163d
Source dataset
uspto-grants-2013_11
Patent number
US08586609B2

Reaction notes

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