Ammonia → 2-Iodo-5-propoxy-benzamide

HRID 330836Notes

Reaction equation

HRID 330836 reaction equation
[OH-].[Na+].C[O:4][C:5](=O)[C:6]1[CH:11]=[C:10]([O:12][CH2:13][CH2:14][CH3:15])[CH:9]=[CH:8][C:7]=1[I:16].Cl.C1N=C[N:21](C(N2C=NC=C2)=O)C=1.N>O.CO>[I:16][C:7]1[CH:8]=[CH:9][C:10]([O:12][CH2:13][CH2:14][CH3:15])=[CH:11][C:6]=1[C:5]([NH2:21])=[O:4]

Participants

8

Reactant 5

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 682631,1'-Carbonyldiimidazole2×HCID 66611398HCID 66611398, compound

Product 1

HCID 666113302-Iodo-5-propoxy-benzamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

129 mL (258 mmol) 2N NaOH are added to 4.12 g (12.9 mmol) methyl-5-propoxy-2-iodobenzoate (XXVII.1) 60 mL MeOH. The mixture is stirred at 50° C. for 3 h. After that time, the mixture was acidified to pH 5 with 1N aq. HCl and extracted with EtOAc (2×). The combined organic layers are washed with water and brine, dried over sodium sulphate and the solvent is removed in vacuo. The crude product is taken up in 30 mL THF and 2.04 g (12.6 mmol) CDI are added. The mixture is stirred at rt for 1 h. Additional 0.5 eq CDI are added and stirring is continued for 20 min. 20 mL of 35% ammonia in water are added and the resulting mixture is stirred at rt for 5 min. The solvent was partly removed in vacuo until precipitation of a white solid. The product is filtered off and dried at 40° C. in vacuo.

Workup

  1. extractionextracted with EtOAc (2×)
  2. washThe combined organic layers are washed with water and brine
  3. dry with materialdried over sodium sulphate
  4. customthe solvent is removed in vacuo
  5. stirringThe mixture is stirred at rt for 1 h
  6. stirringstirring
  7. waitis continued for 20 min
  8. stirringthe resulting mixture is stirred at rt for 5 min
  9. customThe solvent was partly removed in vacuo until precipitation of a white solid
  10. filtrationThe product is filtered off
  11. customdried at 40° C. in vacuo

Sources & evidence

ORD record
ord-a8804ced20064a5292cf2fa3ed078121
Source dataset
uspto-grants-2014_11
Patent number
US08877754B2

Reaction notes

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