4-Chlorophenyl Isocyanate → HCID 178522069, compound

HRID 455008Notes

Reaction equation

HRID 455008 reaction equation
[NH2:1][C:2]1[S:21][C:5]2[CH2:6][N:7]([C:10]([C:12]3[CH:20]=[CH:19][C:15]4[NH:16][N:17]=[N:18][C:14]=4[CH:13]=3)=[O:11])[CH2:8][CH2:9][C:4]=2[C:3]=1[C:22]([N:24]1[CH2:28][CH2:27][CH2:26][CH2:25]1)=[O:23].[Cl:29][C:30]1[CH:35]=[CH:34][C:33]([N:36]=[C:37]=[O:38])=[CH:32][CH:31]=1>N1C=CC=CC=1.CS(C)=O>[NH:16]1[C:15]2[CH:19]=[CH:20][C:12]([C:10]([N:7]3[CH2:8][CH2:9][C:4]4[C:3]([C:22]([N:24]5[CH2:28][CH2:27][CH2:26][CH2:25]5)=[O:23])=[C:2]([NH:1][C:37]([NH:36][C:33]5[CH:34]=[CH:35][C:30]([Cl:29])=[CH:31][CH:32]=5)=[O:38])[S:21][C:5]=4[CH2:6]3)=[O:11])=[CH:13][C:14]=2[N:18]=[N:17]1

Participants

5

Reactant 2

HCID 76934-Chlorophenyl Isocyanate2×HCID 178509323HCID 178509323, compound

Product 1

HCID 178522069HCID 178522069, compoundYield 4%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 1049PyridineSolvent

Procedure

Starting material 13 (1.2 g, 20% content, 0.6 mmol) was dissolved in 5 ml pyridine and one half of 112 mg (0.7 mmol) p-chlorphenyl isocyanate was added. The reaction mixture was stirred over night at ambient temperature. Then the other half of the p-chlorphenyl isocyanate was added and the reaction was again stirred over night at ambient temperature. The reaction was now concentrated in vacuo and the thereby isolated crude product was dissolved in 7 ml DMSO and purified by prep. HPLC (Method 3). The pure fractions were combined, the solvent reduced and the product finally lyophilized. The desired product 14 could thereby be isolated as yellow solid (16.2 mg, 4%; and additional 17 mg, 84% content 14, 4% yield).

Workup

  1. stirringthe reaction was again stirred over night at ambient temperature
  2. concentrationThe reaction was now concentrated in vacuo
  3. customthe thereby isolated crude product
  4. custompurified by prep

Sources & evidence

ORD record
ord-e07c489b868d43459ef11cfd7f816651
Source dataset
uspto-grants-2013_07
Patent number
US08497283B2

Reaction notes

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