Citric Acid → HCID 28384692, compound

HRID 1752860Notes

Reaction equation

HRID 1752860 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([S:10](Cl)(=[O:12])=[O:11])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].C(N(CC)CC)C.[C:21]([NH2:25])([CH3:24])([CH3:23])[CH3:22].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([S:10]([NH:25][C:21]([CH3:24])([CH3:23])[CH3:22])(=[O:12])=[O:11])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 6385Tert-ButylamineHCID 8471TriethylamineHCID 38637473-bromo-4-methoxybenzenesulfonyl chloride

Product 1

HCID 28384692HCID 28384692, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-Bromo-4-methoxyphenylsulfonyl chloride (2.80 g, 9.8 mmol) was dissolved in dichloromethane (30 mL) and the solution was treated with triethylamine (1.76 mL, 12.6 mmol), followed by the dropwise addition of t-butylamine (1.33 mL, 12.6 mmol). The mixture was allowed to stand for 2 hours and then was poured onto a mixture of 5% citric acid solution and dichloromethane. The organic layer was separated and the aqueous layer was extracted with dichloromethane (×2). The combined organic layers were dried and concentrated. Crystallization of the crude solid from ethyl acetate/hexane gave 3-bromo-N-tert-butyl-4-methoxybenzenesulfonamide (2.43 g, 77%).

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with dichloromethane (×2)
  3. customThe combined organic layers were dried
  4. concentrationconcentrated
  5. customCrystallization of the crude solid from ethyl acetate/hexane

Sources & evidence

ORD record
ord-6b45e4d7918b412d892aa4afc7831b29
Source dataset
uspto-grants-2015_10
Patent number
US09162986B2

Reaction notes

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