Ethyl isocyanate → HCID 10732267, compound

HRID 2292691Notes

Reaction equation

HRID 2292691 reaction equation
[CH2:1]([N:3]=[C:4]=[O:5])[CH3:2].[NH2:6][C:7]1[CH:8]=[C:9]([C:18]([CH3:21])([CH3:20])[CH3:19])[C:10]2[O:14][CH2:13][C:12]([CH3:16])([CH3:15])[C:11]=2[CH:17]=1>CCOCC>[C:18]([C:9]1[C:10]2[O:14][CH2:13][C:12]([CH3:15])([CH3:16])[C:11]=2[CH:17]=[C:7]([NH:6][C:4]([NH:3][CH2:1][CH3:2])=[O:5])[CH:8]=1)([CH3:21])([CH3:20])[CH3:19]

Participants

4

Reactant 2

HCID 8022Ethyl isocyanateHCID 106804065-Amino-7-tert-butyl-2,3-dihydro-3,3-dimethylbenzofuran

Product 1

HCID 10732267HCID 10732267, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Ethylisocyanate (0.18 mL, 2.28 mmol) is added dropwise to a solution of 5-amino-7-tert-butyl-2,3-dihydro-3,3-dimethylbenzofuran (500 mg, 2.28 mmol) in 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 a tan solid (657 mg). This solid is recrystallized from EtOAc to give the title compound as white prisms (335 mg, 51%), mp=197°-198° 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 a tan solid (657 mg)
  5. customThis solid is recrystallized from EtOAc

Sources & evidence

ORD record
ord-125695e6eec14830b51b39143427a0f7
Source dataset
uspto-grants-1997_11
Patent number
US05684041

Reaction notes

Loading…