Methyl Isocyanate → N-(7-tert-Butyl-2,3-dihydro-3,3-dimethyl-5-benzofuranyl)-N'-methyl urea

HRID 2292690Notes

Reaction equation

HRID 2292690 reaction equation
[CH3:1][N:2]=[C:3]=[O:4].[NH2:5][C:6]1[CH:7]=[C:8]([C:17]([CH3:20])([CH3:19])[CH3:18])[C:9]2[O:13][CH2:12][C:11]([CH3:15])([CH3:14])[C:10]=2[CH:16]=1>CCOCC>[C:17]([C:8]1[C:9]2[O:13][CH2:12][C:11]([CH3:14])([CH3:15])[C:10]=2[CH:16]=[C:6]([NH:5][C:3]([NH:2][CH3:1])=[O:4])[CH:7]=1)([CH3:20])([CH3:19])[CH3:18]

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 106804065-Amino-7-tert-butyl-2,3-dihydro-3,3-dimethylbenzofuran

Product 1

HCID 9925571N-(7-tert-Butyl-2,3-dihydro-3,3-dimethyl-5-benzofuranyl)-N'-methyl ureaYield 56%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Methylisocyanate (0.14 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 over 0.5 h and the reaction is quenched with H2O (10 mL) after 1 h. The reaction is extracted with Et2O (3×10 mL) and the organic layers dried (MgSO4) and evaporated to a tan solid (550 mg). This solid is recrystallized from EtOAc to give the product as white prisms (350 mg, 56%), mp=193°-194° C.

Workup

  1. customthe reaction is quenched with H2O (10 mL) after 1 h
  2. extractionThe reaction is extracted with Et2O (3×10 mL)
  3. dry with materialthe organic layers dried (MgSO4)
  4. customevaporated to a tan solid (550 mg)
  5. customThis solid is recrystallized from EtOAc

Sources & evidence

ORD record
ord-1446b53a33b9453796f04143f2265837
Source dataset
uspto-grants-1997_11
Patent number
US05684041

Reaction notes

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