Isopropylamine → HCID 11242707, compound

HRID 1857477Notes

Reaction equation

HRID 1857477 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[N:18][C:19]#[N:20])OC2C=CC=CC=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[CH:21]([NH2:24])([CH3:23])[CH3:22]>>[C:19]([NH:18][C:10]([NH:9][C:4]1[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[CH:3]=1)=[N:24][CH:21]([CH3:23])[CH3:22])#[N:20]

Participants

3

Reactant 2

HCID 6363IsopropylamineHCID 178512268HCID 178512268, compound

Product 1

HCID 11242707HCID 11242707, compoundYield 43%

Procedure

N-(3,5-Dichlorophenyl)-N'-cyano-O-phenylisourea (0.98 mmol, 300 mg) and isopropylamine (1 ml) was stirred in a sealed flask for 19 h at 75° C. After concentration the residue was dissolved in dichloromethane, washed with 1 N aqueous HCl (2×), water, dried (Na2SO4) and concentrated. The residue was crystallized from ethyl acetate/heptane 1:3 to give the title compound (115 mg, 43%) as white crystals. Mp 156-158.5° C.; 1H-NMR (CDCl3): δ 1.21 (d, 6H), 4.03 (m,1H), 4.70 (br d,1H), 7.16 (m, 2H), 7.29 (m,1H), 7.47 ppm (br,1H); MA calc for C11H12Cl2N4 : C, 48.73%; H, 4.46%; N, 20.66%. Found: C, 48.76%; H, 4.49%; N, 20.38%.

Workup

  1. concentrationAfter concentration the residue
  2. dissolutionwas dissolved in dichloromethane
  3. washwashed with 1 N aqueous HCl (2×), water
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was crystallized from ethyl acetate/heptane 1:3

Sources & evidence

ORD record
ord-0dd6776c3d97439780c57e86d3b89e19
Source dataset
uspto-grants-2000_11
Patent number
US06147098

Reaction notes

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