Dimethylcarbamoyl Chloride → HCID 53739838, compound

HRID 1757453Notes

Reaction equation

HRID 1757453 reaction equation
[I:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.C([N:11]([CH2:14]C)[CH2:12]C)C.[CH3:16][N:17](C)[C:18](Cl)=[O:19].C(OCC)(=[O:24])C.CCCCC>C(Cl)Cl>[CH3:12][NH:11][C:14]([N:6]([C:5]1[CH:7]=[CH:8][C:2]([I:1])=[CH:3][CH:4]=1)[C:18]([NH:17][CH3:16])=[O:19])=[O:24]

Participants

6

Reactant 4

HCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 108934-IodoanilineHCID 22335286Ethyl acetate pentane

Product 1

HCID 53739838HCID 53739838, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-iodoaniline (4.22 g, 19.3 mmol), triethylamine (2.78 mL), and dimethylcarbamoyl chloride (1.86 mL) in CH2Cl2 (100 mL) wasstirred for 1 hour at ambient temperature and 2 hours at 80° C., during which time the CH2Cl2 evaporated. The residue was left standing at ambient temperature for 36 hours and was then partitioned between ethyl acetate (200 mL), and H2O (100 mL). The layers were separated and the organic phase was dried over MgSO4, filtered, and concentrated in vacuo to give a solid. The crude solid was washed with 1:1ethyl acetate/pentane to give 4-(N',N'-dimethylaminocarbonylamino)-iodobenzene (3.2 g, 55% yield). 1H NMR (300 MHz, DMSO-d6) d 8.36 (1H, s), 7.54 (2H, dt, J=9.0, 1.5 Hz), 7.35 (2H, dr, J=9.0, 1.5 Hz), 2.91 (6H, s). MS rn/e 291 (M+H)+, 308 (M+NH4)+.

Workup

  1. customthe CH2Cl2 evaporated
  2. waitThe residue was left
  3. waitstanding at ambient temperature for 36 hours
  4. customwas then partitioned between ethyl acetate (200 mL), and H2O (100 mL)
  5. customThe layers were separated
  6. dry with materialthe organic phase was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto give a solid
  10. washThe crude solid was washed with 1

Sources & evidence

ORD record
ord-0774ae6af04e4902942095f20e6f172b
Source dataset
uspto-grants-1995_08
Patent number
US05446062

Reaction notes

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