Diphosgene → HCID 22348338, compound

HRID 916565Notes

Reaction equation

HRID 916565 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([S:8]([C:11]2[CH:17]=[CH:16][C:14]([NH2:15])=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH2:4][CH2:3]1.Cl[C:19]([O:22]C(Cl)=O)(Cl)Cl>C1C=CC=CC=1>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([S:8]([C:11]2[CH:17]=[CH:16][C:14]([N:15]=[C:19]=[O:22])=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 10426DiphosgeneHCID 5672614-(4-Methylpiperazine-1-sulfonyl)aniline

Product 1

HCID 22348338HCID 22348338, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

4-(4-Methylpiperazin-1-sulfonyl)aniline (0.5 g, 1.96 mmol) dissolved in anhydrous benzene was added dropwise to a solution of trichloromethylchloroformate (0.3 mL, 2.35 mmol) in anhydrous benzene at −10° C. The mixture was warmed to room temperature for 10 minutes, then heated to 90° C. for 2 h. The mixture was concentrated under reduced pressure to provide 4-[(4-methylpiperazin-1-yl)sulfonyl]phenyl isocyanate as a solid, used as an intermediate in the production of Compound 105. IR: 1166, 1339, 2265 cm−1.

Workup

  1. temperatureheated to 90° C. for 2 h
  2. concentrationThe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-1ab7edbb421c4a6696798b2ebbb0a636
Source dataset
uspto-grants-2007_09
Patent number
US07271171B2

Reaction notes

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