Dichloromethane → HCID 66772853, compound

HRID 339406Notes

Reaction equation

HRID 339406 reaction equation
[CH3:1][CH2:2][CH2:3][CH:4]([NH2:8])[CH2:5][CH2:6][CH3:7].Cl[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[N:16]=[C:17]=[O:18].C(Cl)[Cl:20]>>[Cl:20][C:14]1[CH:13]=[CH:12][C:11]([NH:16][C:17]([NH:8][CH:4]([CH2:5][CH2:6][CH3:7])[CH2:3][CH2:2][CH3:1])=[O:18])=[CH:10][CH:15]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 386654-HeptanamineHCID 76833Chlorophenyl isocyanate

Product 1

HCID 66772853HCID 66772853, compoundYield 67%

Procedure

To a solution of heptan-4-amine (0.18 mL, 1 mmol) in CH2Cl2 (5 mL) was added 1-chloro-2-isocyanatobenzene (0.12 mL, 1 mmol) at room temperature. The reaction mixture was stirred for 2 h. A white solid was precipitated out. The reaction mixture was filtered. The solid was washed with CH2Cl2 to afford 1-(4-chlorophenyl)-3-(heptan-4-yl)urea (180 mg, 67%) as a white solid. mp: 135-136° C. 1H NMR (500 MHz, CDCl3): δ 0.93 (t, 6H), 1.45 (m, 6H), 1.53 (m, 2H), 3.80 (br s, 1H), 4.33 (d, 1H), 6.00 (s, 1H), 6.95 (td, 1H), 7.23 (dt, 1H), 7.33 (dd, 1H), 8.13 (dd, 1H). MS (M+H, 269).

Workup

  1. customA white solid was precipitated out
  2. filtrationThe reaction mixture was filtered
  3. washThe solid was washed with CH2Cl2

Sources & evidence

ORD record
ord-242004e78cd047f0858dc337cdf9c596
Source dataset
uspto-grants-2014_11
Patent number
US08895050B2

Reaction notes

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