Bromoacetyl bromide → N-[4-(aminosulfonyl)-2-chlorophenyl]-2-bromoAcetamide

HRID 1157390Notes

Reaction equation

HRID 1157390 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH2:11])(=[O:10])=[O:9])=[CH:4][C:3]=1[Cl:12].C(=O)(O)[O-].[Na+].[Br:18][CH2:19][C:20](Br)=[O:21]>C(Cl)Cl>[NH2:11][S:8]([C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:20](=[O:21])[CH2:19][Br:18])=[C:3]([Cl:12])[CH:4]=1)(=[O:9])=[O:10]

Participants

5

Reactant 3

HCID 61147Bromoacetyl bromideHCID 516892Sodium BicarbonateHCID 15020144-Amino-3-chlorobenzenesulfonamide

Product 1

HCID 59511722N-[4-(aminosulfonyl)-2-chlorophenyl]-2-bromoAcetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 750 mg (3.63 mmol) of 4-amino-3-chlorobenzenesulfonamide (A-2) and 610 mg (7.26 mmol) of sodium bicarbonate in 25 mL of CH2Cl2 was stirred at room temperature for 18 hours. Bromoacetyl bromide (A-1) was then added, and the mixture was stirred for an additional 12 hours. The mixture was then concentrated in vacuo to a yellow oil. The oil was washed with three 25 mL portions of diethyl ether, decanted, and concentrated in vacuo to give the desired product A-3 as a tan solid. MS: M+1=329.0.

Workup

  1. stirringthe mixture was stirred for an additional 12 hours
  2. concentrationThe mixture was then concentrated in vacuo to a yellow oil
  3. washThe oil was washed with three 25 mL portions of diethyl ether
  4. customdecanted
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b0b60f6f4238438b970beae9d54a4270
Source dataset
uspto-grants-2010_10
Patent number
US07807684B2

Reaction notes

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