Propylamine → 2-Amino-5-iodo-N-propylbenzamide

HRID 1276620Notes

Reaction equation

HRID 1276620 reaction equation
[CH2:1]([NH2:4])[CH2:2][CH3:3].[I:5][C:6]1[CH:7]=[CH:8][C:9]2[NH:14]C(=O)O[C:11](=[O:16])[C:10]=2[CH:17]=1>N1C=CC=CC=1>[NH2:14][C:9]1[CH:8]=[CH:7][C:6]([I:5])=[CH:17][C:10]=1[C:11]([NH:4][CH2:1][CH2:2][CH3:3])=[O:16]

Participants

4

Reactant 2

HCID 7852PropylamineHCID 2944806-iodo-2H-3,1-benzoxazine-2,4(1H)-dione

Product 1

HCID 221165242-Amino-5-iodo-N-propylbenzamideYield 74.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Propylamine (1.2 g, 20.3 mmol) and 6-iodo-2H-3,1-benzoxazine-2,4(1H)-dione (5.0 g, 17.3 mmol) were combined in pyridine (85 mL) and stirred at room temperature for 24 h. The reaction was concentrated under reduced pressure and the resulting residue was partitioned between ethyl acetate (200 mL) and 5% hydrochloric acid (200 mL). The phases were separated and the organic phase was washed with 1N sodium hydroxide, water, and brine. Drying over anhydrous sodium sulfate and evaporation under reduced pressure afforded 3.9 g of the title compound, 1H NMR (300 MHz, CDCl3): δ0.99 (t,3H1); 1.63 (m,2H); 3.35 (m,2H); 5.52 (br s,2H); 5.95 (br s,1H); 6.47 (d, 1H); 7.42 (dd,1H); 7.55(d,1H).

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. customthe resulting residue was partitioned between ethyl acetate (200 mL) and 5% hydrochloric acid (200 mL)
  3. customThe phases were separated
  4. washthe organic phase was washed with 1N sodium hydroxide, water, and brine
  5. dry with materialDrying over anhydrous sodium sulfate and evaporation under reduced pressure

Sources & evidence

ORD record
ord-ba8aa42850ad44af9b79907d0b0c5476
Source dataset
uspto-grants-2000_12
Patent number
US06166208

Reaction notes

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