4-Chlorophenyl Isocyanate → HCID 9803432, compound

HRID 602321Notes

Reaction equation

HRID 602321 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[O:10])=[CH:4][CH:3]=1.Cl.[O:12]=[C:13]1[CH2:18][O:17][CH2:16][CH2:15][N:14]1[C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26]([CH:28]2[CH2:32][CH2:31][CH2:30][NH:29]2)=[O:27])=[CH:21][CH:20]=1.C(N(CC)CC)C>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([N:29]2[CH2:30][CH2:31][CH2:32][C@@H:28]2[C:26]([NH:25][C:22]2[CH:21]=[CH:20][C:19]([N:14]3[CH2:15][CH2:16][O:17][CH2:18][C:13]3=[O:12])=[CH:24][CH:23]=2)=[O:27])=[O:10])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 76934-Chlorophenyl IsocyanateHCID 8471TriethylamineHCID 66593188HCID 66593188, compound

Product 1

HCID 9803432HCID 9803432, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.3 95 mg (0.61 mmol) of 4-chlorophenyl isocyanate are added to a solution of 200 mg (0.61 mmol) of N-[4-(3-oxomorpholin-4-yl)phenyl]pyrrolidine-2-carboxamide hydrochloride and 1 ml of triethylamine in 5 ml of methylene chloride, and the reaction solution is stirred at room temperature for two hours. The reaction solution is subsequently washed with 5 ml of 1N hydrochloric acid and 5 ml of water, and the methylene chloride solution is dried over sodium sulfate. After the solvent has been stripped off under reduced pressure, the crude product is recrystallised from ethanol/diethyl ether, giving 120 mg of the title compound (“A1”) as a white powder; ESI 443; m.p. 227.6°.

Workup

  1. washThe reaction solution is subsequently washed with 5 ml of 1N hydrochloric acid and 5 ml of water
  2. dry with materialthe methylene chloride solution is dried over sodium sulfate
  3. customthe crude product is recrystallised from ethanol/diethyl ether

Sources & evidence

ORD record
ord-6a037f2a31d44c2aa9d90d7ce671b37f
Source dataset
uspto-grants-2011_03
Patent number
US07906516B2

Reaction notes

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