4-Chlorophenyl Isocyanate → HCID 59361401, compound

HRID 888892Notes

Reaction equation

HRID 888892 reaction equation
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[N:11]1[C:14](=[O:15])[C:13]([CH3:17])([CH3:16])[NH:12]1)[CH2:8]2.[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([N:25]=[C:26]=[O:27])=[CH:21][CH:20]=1.C(N(CC)CC)C>ClCCl.CN(C1C=CN=CC=1)C>[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26]([N:12]2[C:13]([CH3:17])([CH3:16])[C:14](=[O:15])[N:11]2[CH:2]2[CH:3]3[CH2:4][CH:5]4[CH2:6][CH:7]([CH2:8][CH:1]2[CH2:10]4)[CH2:9]3)=[O:27])=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 76934-Chlorophenyl IsocyanateHCID 8471TriethylamineHCID 673028822-(Adamantan-2-yl)-4,4-dimethyl-1,2-diazetidin-3-one

Product 1

HCID 59361401HCID 59361401, compoundYield 100.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 2-(adamantan-2-yl)-4,4-dimethyl-1,2-diazetidin-3-one (30.0 mg, 0.128 mmol) prepared in Process 3 of Example 12 in dichloromethane (3 mL) was added sequentially with 4-chlorophenyl isocyanate (19.7 mg, 0.128 mmol), triethylamine (19.4 mg, 0.192 mmol), DMAP (catalyst amount) at room temperature, and the resultant was stirred at the same temperature for 1.5 hours. The reaction solution was filtered using celite, concentrated in vacuo, and the obtained residue was purified using Preparatory Thin-Layer chromatography (hexane:ethyl acetate=2:1), and the title compound (49.7 mg, 100%) was obtained as a white crystalline powder.

Workup

  1. filtrationThe reaction solution was filtered
  2. concentrationconcentrated in vacuo
  3. customthe obtained residue was purified

Sources & evidence

ORD record
ord-87e0fa42be32487292fff9e9fc9b7c29
Source dataset
uspto-grants-2012_08
Patent number
US08252781B2

Reaction notes

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