3-(Methylthio)propylamine → 2-amino-3-iodo-N-(3-(methylthio)propyl)benzamide

HRID 1056413Notes

Reaction equation

HRID 1056413 reaction equation
[NH2:1][C:2]1[C:10]([I:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[CH3:12][S:13][CH2:14][CH2:15][CH2:16][NH2:17].CCN(C(C)C)C(C)C.CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O>CCOC(C)=O>[NH2:1][C:2]1[C:10]([I:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH:17][CH2:16][CH2:15][CH2:14][S:13][CH3:12])=[O:6]

Participants

6

Reactant 4

HCID 777433-(Methylthio)propylamineHCID 81531DiisopropylethylamineHCID 111923Propylphosphonic anhydrideHCID 2820702-Amino-3-iodobenzoic acid

Product 1

HCID 897819962-amino-3-iodo-N-(3-(methylthio)propyl)benzamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a 100-mL round-bottomed flask was added 2-amino-3-iodobenzoic acid (1.50 g, 5.70 mmol, Bosche Scientific) and 3-(methylthio)propylamine (0.72 mL, 6.84 mmol, Acros) in EtOAc (15 mL) followed by DIEA (1.19 mL, 6.84 mmol) and 1-propanephosphonic acid cyclic anhydride (3.99 mL, 6.27 mmol, 50% in EtOAc, Sigma Aldrich). The reaction was stirred at RT for 4 h, and then quenched with sat. NaHCO3. The layers were separated and the organic layer was washed with sat. NaHCO3, brine, then dried (MgSO4), filtered and concentrated to give the crude product. MS (ESI, pos. ion) m/z: 350.9 (M+1); 1H NMR (400 MHz, CDCl3) δ ppm 7.74 (1H, dd, J=7.6, 1.4 Hz), 7.30 (1H, dd, J=7.8, 1.4 Hz), 6.41 (1H, t, J=7.8 Hz), 6.32 (1H, br. s.), 3.54 (2H, q, J=6.7 Hz), 2.61 (2H, t, J=6.9 Hz), 2.09-2.17 (3H, m), 1.92 (2H, quin, J=6.8 Hz)

Workup

  1. customquenched with sat. NaHCO3
  2. customThe layers were separated
  3. washthe organic layer was washed with sat. NaHCO3, brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e71db6f44bf8468ca2286fe0ccaff5d9
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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