Diethyl azodicarboxylate → HCID 135830955, compound

HRID 1824784Notes

Reaction equation

HRID 1824784 reaction equation
[Cl:1][C:2]1[CH:20]=[C:19]([O:21]C)[CH:18]=[CH:17][C:3]=1[C:4]([NH:6][C:7]1[C:12]([OH:13])=[CH:11][C:10]([O:14]C)=[CH:9][C:8]=1[Cl:16])=O.CCOC(/N=N/C(OCC)=O)=O>C1COCC1.C(OCC)(=O)C>[Cl:16][C:8]1[C:7]2[N:6]=[C:4]([C:3]3[CH:17]=[CH:18][C:19]([OH:21])=[CH:20][C:2]=3[Cl:1])[O:13][C:12]=2[CH:11]=[C:10]([OH:14])[CH:9]=1

Participants

5

Reactant 2

HCID 5462977Diethyl azodicarboxylateHCID 22144502HCID 22144502, compound

Product 1

HCID 135830955HCID 135830955, compoundYield 92.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

2-Chloro-N-(2-chloro-6-hydroxy-4-methoxy-phenyl)-4-methoxy-benzamide (40 mg) was completely dissolved in THF (5 mL) and PPH3 (46 mg) was added and the mixture was stirred until all PPH3 dissolved. To this mixture was added drop wise DEAD (0.03 mL) diluted in THF (0.5 mL). The mixture was stirred at room temperature for 2 h and the reaction mixture was diluted with ethyl acetate and washed with water, brine, dried over MgSO4 and concentrated. Flash chromatography on silica gel eluting with 10% to 30% ethyl acetate-hexane afforded 32 mg (85%) of the title compound as a solid. MS: 324 (MH+), HPLC tR: 3.18 min.

Workup

  1. additionPPH3 (46 mg) was added
  2. dissolutiondissolved
  3. stirringThe mixture was stirred at room temperature for 2 h
  4. washwashed with water, brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-26e1231cb28d41598882a5362e736e5f
Source dataset
uspto-grants-2006_05
Patent number
US07045539B2

Reaction notes

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