N-bromobutanimide → HCID 12067430, compound

HRID 352988Notes

Reaction equation

HRID 352988 reaction equation
[Br:1]N1C(=O)CCC1=O.[OH:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:12][CH:11]=1>C(Cl)(Cl)Cl>[Br:1][C:15]1[CH:14]=[C:13]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:20])([CH3:22])[CH3:21])[CH:12]=[CH:11][C:10]=1[OH:9]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 2756771N-Boc-4-hydroxyaniline

Product 1

HCID 12067430HCID 12067430, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of 9.4 g (52.8 mmoles) of N-bromosuccinimide in 450 mL of chloroform was added dropwise to a suspension 10 g (47.8 mmoles) of tert.butyl N-(4-hydroxy-phenyl)carbamate in 100 mL of chloroform at 0° C. over a period of 2 hours. The reaction mixture was stirred for an additional 15 min and then washed twice with water (first with 400 mL, then with 200 mL), dried over magnesium sulfate, filtered and partly evaporated. Hexane was added to the residue with stirring which caused the formation of a precipitate. The precipitate was filtered off and washed with hexane.

Workup

  1. washwashed twice with water (first with 400 mL
  2. dry with materialwith 200 mL), dried over magnesium sulfate
  3. filtrationfiltered
  4. custompartly evaporated
  5. additionHexane was added to the residue
  6. stirringwith stirring which
  7. filtrationThe precipitate was filtered off
  8. washwashed with hexane

Sources & evidence

ORD record
ord-59541b35f6f3464a974fbcb6660b90d6
Source dataset
uspto-grants-2004_06
Patent number
US06749644B2

Reaction notes

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