Propyl isocyanate → N-(7-tert-Butyl-2,3-dihydro-3,3-dimethyl-5-benzofuranyl)-N'-propyl urea

HRID 2292692Notes

Reaction equation

HRID 2292692 reaction equation
[CH2:1]([N:4]=[C:5]=[O:6])[CH2:2][CH3:3].[C:7]([C:11]1[C:19]2[O:18][CH2:17][C:16]([CH3:21])([CH3:20])[C:15]=2[CH:14]=[C:13]([NH2:22])[CH:12]=1)([CH3:10])([CH3:9])[CH3:8]>CCOCC>[C:7]([C:11]1[C:19]2[O:18][CH2:17][C:16]([CH3:21])([CH3:20])[C:15]=2[CH:14]=[C:13]([NH:22][C:5]([NH:4][CH2:1][CH2:2][CH3:3])=[O:6])[CH:12]=1)([CH3:10])([CH3:8])[CH3:9]

Participants

4

Reactant 2

HCID 61033Propyl isocyanateHCID 106804065-Amino-7-tert-butyl-2,3-dihydro-3,3-dimethylbenzofuran

Product 1

HCID 10709657N-(7-tert-Butyl-2,3-dihydro-3,3-dimethyl-5-benzofuranyl)-N'-propyl ureaYield 39%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Propylisocyanate (0.21 mL, 2.28 mmol) is added dropwise to a solution of (7-t-butyl-2,3-dihydro-3,3-dimethyl-5-benzofuranyl)-amine (500 mg, 2.28 mmol) and Et2O (5 mL). A solid forms after 10 min and the reaction is quenched with H2O (10 mL) after 40 min. The reaction is extracted with Et2O (3×10 mL) and the organic layers dried (MgSO4) and evaporated to an off-white solid (650 mg). This solid is recrystallized from EtOAc to give a white solid (270 mg, 39%), mp=193°-194° C.

Workup

  1. customthe reaction is quenched with H2O (10 mL) after 40 min
  2. extractionThe reaction is extracted with Et2O (3×10 mL)
  3. dry with materialthe organic layers dried (MgSO4)
  4. customevaporated to an off-white solid (650 mg)
  5. customThis solid is recrystallized from EtOAc

Sources & evidence

ORD record
ord-f158a86d17084085ab7fb18602530a20
Source dataset
uspto-grants-1997_11
Patent number
US05684041

Reaction notes

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