Phosgene → HCID 19024454, compound

HRID 1033801Notes

Reaction equation

HRID 1033801 reaction equation
[CH2:1]([NH:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[S:19](=[O:26])(=[O:25])[NH:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH3:4].[OH-].[Na+].[C:29](Cl)([Cl:31])=[O:30]>C1(C)C=CC=CC=1>[CH2:1]([N:5]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[S:19](=[O:25])(=[O:26])[NH:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:9][CH:8]=1)[C:29]([Cl:31])=[O:30])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 14798Sodium HydroxideHCID 19024413HCID 19024413, compound

Product 1

HCID 19024454HCID 19024454, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 1.8 g (4.81 mmole) of N-butyl-N-[[2'-(N-t-butylsulfamoyl)biphenyl-4-yl]methyl]amine (from Step E) in 35 mL of toluene was cooled to -5° C. and treated with 9.6 mL (24 mmole) of 2.5M sodium hydroxide (aqueous), followed by 7.5 mL (14.5 mmole) of phosgene in toluene. The cold mixture was stirred for 45 minutes and then filtered to remove a white precipitate. The layers of the filtrate were separated, and the toluene phase was concentrated in vacuo to yield 1.21 g (58%) of the title compound as a white solid, mp 128°-129° C.; homogeneous by TLC (3:1 hexane-EtOAc); IR spectrum νCO 1745 cm-1 ; FAB-MS m/e 438 (M+1)+. The 1H NMR spectrum indicated the presence of two rotameric forms.

Workup

  1. filtrationfiltered
  2. customto remove a white precipitate
  3. customThe layers of the filtrate were separated
  4. concentrationthe toluene phase was concentrated in vacuo

Sources & evidence

ORD record
ord-ed5582380fab4796a6e354b44d111d91
Source dataset
uspto-grants-1994_05
Patent number
US05312820

Reaction notes

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