Thiophosgene → HCID 22040478, compound

HRID 2070332Notes

Reaction equation

HRID 2070332 reaction equation
F[C:2]1[C:7]([N:8]2[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]2)=[CH:6][CH:5]=[C:4]([N+:15]([O-])=O)[C:3]=1[NH2:18].C(=O)([O-])[O-].[Na+].[Na+].C(Cl)(Cl)=S>CC(C)=O>[CH:14]1([N:11]2[CH2:12][CH2:13][N:8]([C:7]3[CH:2]=[C:3]([NH2:18])[C:4]([NH2:15])=[CH:5][CH:6]=3)[CH2:9][CH2:10]2)[CH2:4][CH2:3][CH2:2][CH2:7]1

Participants

5

Reactant 3

HCID 10040ThiophosgeneHCID 10340Sodium CarbonateHCID 220408162-Fluoro-3-(4-methyl-piperazin-1-yl)-6-nitro-phenylamine

Product 1

HCID 22040478HCID 22040478, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 1 (1 eq) and sodium carbonate (1.5 eq) in acetone was stirred in an ice bath under an atmosphere of nitrogen. Thiophosgene (1.5 eq) was added drop wise over 30 minutes. The reaction was stirred for another 30 minutes in the ice bath before being removed and allowed to warm to RT. The reaction was stirred at RT for 1.5 h before the reaction solution was concentrated under vacuum. Toluene was added to the crude product and removed under vacuum to azetrope off any residual thiophosgene and afford the product 2. MS: MH+=219

Workup

  1. custombefore being removed
  2. concentrationwas concentrated under vacuum
  3. additionToluene was added to the crude product
  4. customremoved under vacuum

Sources & evidence

ORD record
ord-51ee0e05b97b4190a75a2417be3fd584
Source dataset
uspto-grants-2012_10
Patent number
US08299108B2

Reaction notes

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