Phosgene → HCID 54019979, compound

HRID 839068Notes

Reaction equation

HRID 839068 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]([C:9]1[CH:16]=[CH:15][C:12]([NH:13][CH3:14])=[CH:11][CH:10]=1)([OH:8])[C:4]([F:7])([F:6])[F:5].C([O-])(O)=O.[Na+].[C:24](Cl)([Cl:26])=[O:25]>CCOCC.O.C1C=CC=CC=1>[CH3:14][N:13]([C:12]1[CH:15]=[CH:16][C:9]([C:3]([OH:8])([C:4]([F:6])([F:5])[F:7])[C:2]([F:17])([F:18])[F:1])=[CH:10][CH:11]=1)[C:24]([Cl:26])=[O:25]

Participants

7

Reactant 3

HCID 6371PhosgeneHCID 516892Sodium BicarbonateHCID 8050151,1,1,3,3,3-Hexafluoro-2-(4-(methylamino)phenyl)propan-2-OL

Product 1

HCID 54019979HCID 54019979, compoundYield 99.5%

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

To a cold (10°) stirred mixture of 137 g (0.50 mole) 4-(hexafluoro-2-hydroxy-2-propyl)-N-methyl aniline in 500 ml Et2O and 168 g (2.0 mole) NaHCO3 in 500 ml H2O add dropwise 500 g (0.6 mole) 12% phosgene in benzene over 1 hour. Add 500 ml Et2O, separate the organic phase, dry, concentrate and wash the residue with hexane to give 167 g white solid; m.p. 152°-154°.

Workup

  1. customseparate the organic phase
  2. customdry
  3. concentrationconcentrate
  4. washwash the residue with hexane

Sources & evidence

ORD record
ord-893850d504c44bf498e70d621c0f5f1e
Source dataset
uspto-grants-1978_06
Patent number
US04093742

Reaction notes

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