Acetic Acid → HCID 86722263, compound

HRID 869417Notes

Reaction equation

HRID 869417 reaction equation
[NH2:1][C:2]1[C:6]2[C:7]([Br:13])=[C:8]([O:11][CH3:12])[CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[C:14](=[O:28])[CH:15]=[CH:16][C:17]1[N:18]=[C:19]([NH:22][C:23](=[O:27])[CH:24]([CH3:26])[CH3:25])[S:20][CH:21]=1.CC#N.CC(O)=O.OP(O)(O)=O>[Cl-].[Cl-].[Zn+2].O>[Br:13][C:7]1[C:6]2[C:2]3[NH:1][CH:16]([C:17]4[N:18]=[C:19]([NH:22][C:23](=[O:27])[CH:24]([CH3:26])[CH3:25])[S:20][CH:21]=4)[CH2:15][C:14](=[O:28])[C:3]=3[O:4][C:5]=2[CH:10]=[CH:9][C:8]=1[O:11][CH3:12]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 1004Phosphoric AcidHCID 6342AcetonitrileHCID 86722262HCID 86722262, compound

Product 1

HCID 86722263HCID 86722263, compoundYield 55.1%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 16A (2 g, 4.3 mmol), ZnCl2 (6 g), MeCN (10 mL), AcOH (2 mL) and H3PO4 (2 mL) was heated to 90° C. and reacted overnight. TLC monitored the reaction. After the reaction completed, the reaction mixture was added dropwise into water, extracted with ethyl acetate and concentrated to give 16B (1.1 g, 55% yield).

Workup

  1. customreacted overnight
  2. customthe reaction
  3. extractionextracted with ethyl acetate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7357f5891e964d5ab3ca22ae9acd37d7
Source dataset
uspto-grants-2015_03
Patent number
US08969373B2

Reaction notes

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