Ammonium Carbonate → 2-(2-Iodophenyl)acetamide

HRID 1778951Notes

Reaction equation

HRID 1778951 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([OH:11])=O.C(=O)([O-])[O-].[NH4+:16].[NH4+]>S(Cl)(Cl)=O>[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([NH2:16])=[O:11]

Participants

4

Reactant 2

HCID 517111Ammonium CarbonateHCID 27800902-Iodophenylacetic acid

Product 1

HCID 184740882-(2-Iodophenyl)acetamide

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 2-iodophenylacetic acid (20.5 g, 78.2 mmol) in thionyl chloride (70 mL) was stirred at 75° C. for 3 hours. The thionyl chloride was removed in vacuo and the resulting residue was dissolved in DCM (100 mL). Ammonium carbonate (15.03 g, 156.5 mmol) was added and the resulting mixture was stirred at 60° C. for 20 hours. The volatiles were evaporated in vacuo, water (100 mL) was added and the resulting suspension was sonicated for 1 minute, before filtering and washing the filter cake with water then Et2O. After air drying, the title compound I6 was obtained as a light cream coloured solid (12.9 g, 63%); 1H NMR (300 MHz, d6-DMSO) δ 7.82 (d, J=8.3 Hz, 1H), 7.41 (brs s, 1H), 7.30-7.37 (m, 2H), 6.95-7.01 (m, 2H), 3.55 (s, 2H). LCMS-B: rt 5.108 min; m/z 262 [M+H]+.

Workup

  1. customThe thionyl chloride was removed in vacuo
  2. dissolutionthe resulting residue was dissolved in DCM (100 mL)
  3. customThe volatiles were evaporated in vacuo, water (100 mL)
  4. additionwas added
  5. customthe resulting suspension was sonicated for 1 minute
  6. filtrationbefore filtering
  7. washwashing the filter cake with water
  8. customAfter air drying

Sources & evidence

ORD record
ord-c5fa446c69f6416cac348e2f004e729e
Source dataset
uspto-grants-2016_02
Patent number
US09266864B2

Reaction notes

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