4-Chlorophenyl Isocyanate → HCID 51037829, compound

HRID 2040434Notes

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:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[N:17]([S:21]([C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][C:25]=1[O:32][CH3:33])(=[O:23])=[O:22])[C:16](=[O:34])[C:15]2([OH:41])[C:35]1[S:36][CH:37]=[CH:38][C:39]=1[CH3:40]>CN(C1C=CN=CC=1)C.C1(C)C=CC=CC=1>[Cl:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[N:17]([S:21]([C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][C:25]=1[O:32][CH3:33])(=[O:23])=[O:22])[C:16](=[O:34])[C:15]2([O:41][C:9](=[O:10])[NH:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)[C:35]1[S:36][CH:37]=[CH:38][C:39]=1[CH3:40]

Participants

Conditions

Temperature: 90 °C

Procedure

4-Chlorophenyl isocyanate (32 mg, 0.208 mmol) and DMAP (5 mg) were successively added to a solution of Example 62 (100 mg, 0.21 mmol) in toluene (20 ml) and stirred at 90° C. for 30 min. The solvent was removed under reduced pressure, and the residue was taken up in ethyl acetate. The organic phase was washed with dilute citric acid solution and saturated sodium chloride solution, dried over magnesium sulfate and concentrated under reduced pressure. Recrystallization from methanol resulted in 80 mg of the desired product.

Workup

customThe solvent was removed under reduced pressure
washThe organic phase was washed with dilute citric acid solution and saturated sodium chloride solution
dry with materialdried over magnesium sulfate
concentrationconcentrated under reduced pressure
customRecrystallization from methanol

Sources & evidence

ORD record: ord-dedc5a63d24041fe85fdd6bbb2c50634
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08580842B2

Reaction notes

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