Bromine → HCID 22222345, compound

HRID 1794605Notes

Reaction equation

HRID 1794605 reaction equation
[CH2:1]([N:8]1[C:13](=[O:14])[C:12]2[C:15]([CH3:18])=[N:16][S:17][C:11]=2[N:10]=[C:9]1[CH2:19][CH2:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:22]Br.CC([O-])=O.[Na+]>C(O)(=O)C>[CH2:1]([N:8]1[C:13](=[O:14])[C:12]2[C:15]([CH3:18])=[N:16][S:17][C:11]=2[N:10]=[C:9]1[CH:19]([Br:22])[CH2:20][CH3:21])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 22222296HCID 22222296, compound

Product 1

HCID 22222345HCID 22222345, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 31 (430 mg, 1.44 mmol), bromine (345 mg, 2.16 mmol) and NaOAc (236 mg, 2.88 mmol) in acetic acid (10 mL) was heated at 40–45° C. for 14 h. The reaction mixture was poured into ice water, a yellow solid was collected by filtration. The crude product 32 was used in the next step without further purification. 1H-NMR (400 MHz, CDCl3): δ 7.06–7.31 (m, 5H), 6.13 (d, J=16.41 Hz, 1H), 4.80 (d, J=16.41 Hz, 1H), 4.56 (t, J=7.26 Hz, 1H), 2.77 (s, 3H), 2.33 (m, 1H), 2.13 (m, 1H), 0.67 (t, J=7.27 Hz, 3H).

Workup

  1. temperaturewas heated at 40–45° C. for 14 h
  2. filtrationa yellow solid was collected by filtration
  3. customThe crude product 32 was used in the next step without further purification

Sources & evidence

ORD record
ord-d539d0e5e8704a27a6087761cc1ca4ff
Source dataset
uspto-grants-2006_04
Patent number
US07022850B2

Reaction notes

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