Hydrochloric Acid → Methyl 3-carbamoyl-5-iodobenzoate

HRID 1055686Notes

Reaction equation

HRID 1055686 reaction equation
Cl.[I:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([C:12]([O:14][CH3:15])=[O:13])[CH:11]=1)[C:6]([O-])=[O:7].[Na+].C(Cl)(=O)C(Cl)=O.C[N:24](C=O)C>O>[C:6]([C:5]1[CH:9]=[C:10]([CH:11]=[C:3]([I:2])[CH:4]=1)[C:12]([O:14][CH3:15])=[O:13])(=[O:7])[NH2:24]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 86690967HCID 86690967, compound

Product 1

HCID 21942671Methyl 3-carbamoyl-5-iodobenzoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

20 ml of 1 M hydrochloric acid were added to a solution of 3.88 g (11.8 mmol) of sodium 3-iodo-5-(methoxycarbonyl)benzoate [J. H. Ackermann et al., J. Med. Chem. 1966, 9 (1), 165-168] in 100 ml of water. After 10 min, the mixture was extracted three times with in each case about 100 ml of ethyl acetate. The combined organic extracts were washed with saturated sodium chloride solution and dried over anhydrous magnesium sulphate. After filtration, the solvent was removed on a rotary evaporator. The residue that remained was dissolved in 75 ml of dichloromethane, and 5.2 ml (59.1 mmol) of oxalyl chloride and a small drop of DMF were added at RT. After 1 h of stirring at RT, all volatile components were removed on a rotary evaporator. The residue was then dissolved in 50 ml of dioxane and, at a temperature of about 0° C., slowly added dropwise to 44 ml of a 25% strength aqueous ammonia solution. After the dropwise addition had ended, the cooling bath was removed and stirring was continued at RT for 30 min. The precipitated product was then filtered off with suction, washed with cold water and dried under high vacuum. This gave 3.02 g (81% of theory, 97% pure) of the title compound.

Workup

  1. extractionthe mixture was extracted three times with in each case about 100 ml of ethyl acetate
  2. washThe combined organic extracts were washed with saturated sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulphate
  4. filtrationAfter filtration
  5. customthe solvent was removed on a rotary evaporator
  6. dissolutionThe residue that remained was dissolved in 75 ml of dichloromethane
  7. customall volatile components were removed on a rotary evaporator
  8. dissolutionThe residue was then dissolved in 50 ml of dioxane and, at a temperature of about 0° C.
  9. additionslowly added dropwise to 44 ml of a 25% strength aqueous ammonia solution
  10. additionAfter the dropwise addition
  11. customthe cooling bath was removed
  12. stirringstirring
  13. waitwas continued at RT for 30 min
  14. filtrationThe precipitated product was then filtered off with suction
  15. washwashed with cold water
  16. customdried under high vacuum

Sources & evidence

ORD record
ord-75c0659a2b7f42a3b5d2f90fb1cd604a
Source dataset
uspto-grants-2016_07
Patent number
US09394309B2

Reaction notes

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