Pyridine → HCID 59377896, compound

HRID 1691829Notes

Reaction equation

HRID 1691829 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([S:9][CH3:10])=[CH:4][C:3]=1[NH2:11].N1C=CC=CC=1.[C:18](Cl)(Cl)=[O:19]>C1(C)C=CC=CC=1.CN(C1C=CN=CC=1)C>[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([S:9][CH3:10])=[CH:4][C:3]=1[N:11]=[C:18]=[O:19]

Participants

6

Reactant 3

HCID 1049PyridineHCID 6371PhosgeneHCID 59377753HCID 59377753, compound

Product 1

HCID 59377896HCID 59377896, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent2×

Procedure

To a solution of 2-bromo-4-chloro-5-methylsulfanyl-phenylamine (0.10 g, 0.396 mmol) in toluene (3 ml) was added pyridine (0.042 ml, 0.515 mmol), DMAP (0.048 g, 0.396 mmol) and 20% phosgene in toluene (0.225 ml, 0.436 mmol). The mixture was stirred at room temperature for two hours, then filtered. The filtrate was concentrated to dryness to give 1-bromo-5-chloro-2-isocyanato-4-methylsulfanyl-benzene (0.095 g) as a white solid that was used directly in the next step.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-f5bcf274ab0f4e3eba37bf2a1c4307cc
Source dataset
uspto-grants-2012_04
Patent number
US08153809B2

Reaction notes

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