2,6-Diisopropylphenyl isocyanate → 1-Chroman-3-yl-3-(2,6-diisopropyl-phenyl)-urea

HRID 1086506Notes

Reaction equation

HRID 1086506 reaction equation
[NH2:1][CH:2]1[CH2:7][C:6]2[CH:8]=[CH:9][CH:10]=[CH:11][C:5]=2[O:4][CH2:3]1.[CH3:12][CH:13]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH:21]([CH3:23])[CH3:22])[C:16]=1[N:24]=[C:25]=[O:26])[CH3:14]>C(OCC)(=O)C>[CH3:14][CH:13]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH:21]([CH3:22])[CH3:23])[C:16]=1[NH:24][C:25]([NH:1][CH:2]1[CH2:7][C:6]2[CH:8]=[CH:9][CH:10]=[CH:11][C:5]=2[O:4][CH2:3]1)=[O:26])[CH3:12]

Participants

4

Reactant 2

HCID 922592,6-Diisopropylphenyl isocyanateHCID 2057093,4-Dihydro-3-amino-2H-1-benzopyran

Product 1

HCID 145552481-Chroman-3-yl-3-(2,6-diisopropyl-phenyl)-ureaYield 59.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3,4-dihydro-3-amino-2H-benzopyran (0.9 g, 6 mmole) in 50 ml of ethyl acetate, there was added 1.22 g (6 mmol) of 2,6-bis(1-methylethyl)phenyl isocyanate. The resulting mixture was stirred at room temperature for twenty hours. The solvent was removed under vacuum and the residue was suspended in 20% ethyl acetate/hexane. The precipitated solid was collected by filtration and dried to yield 1.25 g of N-[2,6-bis-(1-methylethyl)phenyl]-N'-(3,4-dihydro-2H-1-benzopyran-3-yl)urea, mp 186°-188° C.

Workup

  1. customThe solvent was removed under vacuum
  2. filtrationThe precipitated solid was collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-d4787c3384e6487d88e98b44870e2b91
Source dataset
uspto-grants-1991_07
Patent number
US05030653

Reaction notes

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