Acetic Acid → HCID 86722256, compound

HRID 869410Notes

Reaction equation

HRID 869410 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:25])/[CH:15]=[CH:16]/[C:17]1[S:21][C:20]([CH:22]([CH3:24])[CH3:23])=[N:19][CH:18]=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[S:21][C:20]([CH:22]([CH3:23])[CH3:24])=[N:19][CH:18]=4)[CH2:15][C:14](=[O:25])[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 86722255HCID 86722255, compound

Product 1

HCID 86722256HCID 86722256, compoundYield 79.1%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 14A (1.4 g, 3.3 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 14B (1.1 g, 78% yield).

Workup

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

Sources & evidence

ORD record
ord-825a036e6540422db76d5b7a45e2bd17
Source dataset
uspto-grants-2015_03
Patent number
US08969373B2

Reaction notes

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