Phosgene → 3-Chloro-4-isocyanatobenzenesulfonamide

HRID 574985Notes

Reaction equation

HRID 574985 reaction equation
[C:1](Cl)(Cl)=[O:2].[NH2:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([NH2:15])(=[O:14])=[O:13])=[CH:8][C:7]=1[Cl:16].C(N(C(C)C)C(C)C)C>ClCCl>[Cl:16][C:7]1[CH:8]=[C:9]([S:12]([NH2:15])(=[O:13])=[O:14])[CH:10]=[CH:11][C:6]=1[N:5]=[C:1]=[O:2]

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 81531DiisopropylethylamineHCID 15020144-Amino-3-chlorobenzenesulfonamide

Product 1

HCID 866536933-Chloro-4-isocyanatobenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a round bottom flask containing a solution of phosgene (1.573 mL) in dichloromethane (5 mL) was added 4-amino-3-chlorobenzenesulfonamide (0.206 g) and N-ethyl-N-isopropylpropan-2-amine (0.521 mL). The resulting clear solution was stirred at room temperature overnight. The mixture was concentrated and further dried under vacuum to provide the title compound.

Workup

  1. concentrationThe mixture was concentrated
  2. customfurther dried under vacuum

Sources & evidence

ORD record
ord-fcd284f0b72a441d803185f2fe936b53
Source dataset
uspto-grants-2015_05
Patent number
US09034875B2

Reaction notes

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