Phosphoric Acid → HCID 86722238, compound

HRID 869389Notes

Reaction equation

HRID 869389 reaction equation
[NH2:1][C:2]1[C:6]2[C:7]([Cl: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.OP(O)(O)=O>[Cl-].[Cl-].[Zn+2].CC(O)=O>[Cl: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

6

Reactant 3

HCID 1004Phosphoric AcidHCID 6342AcetonitrileHCID 86722237HCID 86722237, compound

Product 1

HCID 86722238HCID 86722238, compoundYield 68.6%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 176Acetic AcidSolvent

Procedure

9A (3.5 g, 9.28 mmol) was added to MeCN (50 mL) and stirred at room temperature. To the mixture was added ZnCl2 (1.91 g, 13.93 mmol, 1.5 eq), followed by AcOH (50 mL) and H3PO4 (50 mL) The reaction mixture was heated to 80° C. and stirred overnight. After reaction completed, the mixture was cooled and poured into crushed ice under stirring, neutralized to pH=7˜8, extracted with ethyl acetate, dried and concentrated to give 2.4 g of product (9B).

Workup

  1. temperaturewas heated to 80° C.
  2. stirringstirred overnight
  3. customAfter reaction
  4. temperaturethe mixture was cooled
  5. additionpoured
  6. custominto crushed ice
  7. stirringunder stirring
  8. extractionextracted with ethyl acetate
  9. customdried
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-cb3a3555d48746bb9b7a6c3cb05bee96
Source dataset
uspto-grants-2015_03
Patent number
US08969373B2

Reaction notes

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