Triethylamine → HCID 10735302, compound

HRID 1272559Notes

Reaction equation

HRID 1272559 reaction equation
[C:1]1([CH3:16])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]([NH2:15])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH3:14].CCN(CC)CC.[Br:24][CH2:25][C:26](Br)=[O:27]>ClCCCl.O>[C:1]1([CH3:16])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH3:14])[NH:15][C:26](=[O:27])[CH2:25][Br:24]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 61147Bromoacetyl bromideHCID 10560454246853-44-1

Product 1

HCID 10735302HCID 10735302, compoundYield 117.8%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 962WaterSolvent

Conditions

Temperature
-78 °C

Procedure

The compound of Example 554F (100 mg, 0.47 mmol) was dissolved in 2 mL of 1,2-dichloroethane. To this solution at −78° C. was added Et3N (0.05 mL) and then dropwise bromoacetyl bromide (40 mL, 0.47 mmol in 1 mL of 1,2-dichloroethane). The reaction mixture was stirred at −78° C. for 10 min, then at r.t. for 2 h., diluted with water (10 mL), and extracted with 1,2-dichloroethane (2×25 mL). The combined organic layers were concentrated to give the bromoacetamide as a white solid (184 mg, 96%) suitable for further use without additional purification.

Workup

  1. waitat r.t. for 2 h.
  2. extractionextracted with 1,2-dichloroethane (2×25 mL)
  3. concentrationThe combined organic layers were concentrated

Sources & evidence

ORD record
ord-b0cf47c7563b427b8a5b7cba2ded6c42
Source dataset
uspto-grants-2007_04
Patent number
US07208517B1

Reaction notes

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