Diethylcarbamoyl chloride → 1,1-Diethyl-3-(6,7,8,9-tetrahydro-dibenzofuran-2-yl)-urea

HRID 1819920Notes

Reaction equation

HRID 1819920 reaction equation
[CH2:1]([N:3]([CH2:7][CH3:8])[C:4](Cl)=[O:5])[CH3:2].[CH:9]1[C:17]2[C:16]3[CH2:18][CH2:19][CH2:20][CH2:21][C:15]=3[O:14][C:13]=2[CH:12]=[CH:11][C:10]=1[NH2:22]>N1C=CC=CC=1.C(Cl)(Cl)Cl>[CH2:1]([N:3]([CH2:7][CH3:8])[C:4]([NH:22][C:10]1[CH:11]=[CH:12][C:13]2[O:14][C:15]3[CH2:21][CH2:20][CH2:19][CH2:18][C:16]=3[C:17]=2[CH:9]=1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 6916Diethylcarbamoyl chlorideHCID 27947826,7,8,9-Tetrahydro-dibenzofuran-2-ylamine

Product 1

HCID 248980751,1-Diethyl-3-(6,7,8,9-tetrahydro-dibenzofuran-2-yl)-ureaYield 54.5%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6212ChloroformSolvent

Procedure

Diethylcarbamoyl chloride (0.72 mL, 5.5 mmol) was added to a solution of 6,7,8,9-tetrahydro-dibenzofuran-2-ylamine (0.94 g, 5.0 mmol) in pyridine (15 mL). The reaction mixture was stirred overnight at room temperature. The crude material was diluted in chloroform and washed with 1 N HCl, water, and brine, dried (Na2SO4) and concentrated. The crude material was recrystallized from acetonitrile to provide 1,1-diethyl-3-(6,7,8,9-tetrahydro-dibenzofuran-2-yl)-urea (0.78 g). Mp 179-180° C.; Anal. Calcd. for C17H22N2O2: C, 71.30; H, 7.74; N, 9.78; Found: C, 71.29; H, 7.66; N, 9.72.

Workup

  1. washwashed with 1 N HCl, water, and brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customThe crude material was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-b5f848d6e7b44f8ba556ec37dba7bf2f
Source dataset
uspto-grants-2009_10
Patent number
US07601856B2

Reaction notes

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