Thiophosgene → Dichloromethane isohexane

HRID 658336Notes

Reaction equation

HRID 658336 reaction equation
[C:1]([Cl:4])([Cl:3])=[S:2].[C:5]([O-])([O-])=O.[K+].[K+].[C:11]([O:15][C:16]1[CH:17]=[C:18]([NH2:23])[CH:19]=[C:20]([F:22])[CH:21]=1)([CH3:14])([CH3:13])[CH3:12]>C(Cl)(Cl)Cl.O>[C:11]([O:15][C:16]1[CH:17]=[C:18]([N:23]=[C:1]=[S:2])[CH:19]=[C:20]([F:22])[CH:21]=1)([CH3:14])([CH3:12])[CH3:13].[Cl:3][CH2:1][Cl:4].[CH3:21][CH2:20][CH2:19][CH:18]([CH3:17])[CH3:5]

Participants

7

Reactant 3

HCID 10040ThiophosgeneHCID 11430Potassium CarbonateHCID 667439143-tert-Butoxy-5-fluoroaniline

Product 2

HCID 86592985Dichloromethane isohexaneHCID 86619831HCID 86619831, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent2×

Procedure

Thiophosgene (33.6 g) in CHCl3 (250 ml) and K2CO3 (64.7 g) in H2O (450 ml) are added, separately and simultaneously, drop wise to a solution of 3-tert-Butoxy-5-fluoro-phenyl-amine (42.9 g) in CHCl3 (350 ml) at 0° C. The reaction mixture is warmed to room temperature over night. The organics are separated and washed with water (3×), brine (1×), dried over MgSO4, filtered and the solvent removed in vacuo. The title compound is obtained by flash column chromatography (silica, eluent dichloromethane/iso-hexane 1:3). 1H nmr (CDCl3, 400 MHz); 6.70 (m, 3H), 1.40 (s, 9H).

Workup

  1. customThe organics are separated
  2. washwashed with water (3×), brine (1×)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-44e73e27702d49a2bd9ab8acc15932c0
Source dataset
uspto-grants-2011_12
Patent number
US08076489B2

Reaction notes

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