Water → HCID 20229663, compound

HRID 1446866Notes

Reaction equation

HRID 1446866 reaction equation
[CH2:1](Br)[C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=O.[CH2:11]([O:15][CH2:16][CH2:17][NH2:18])[CH2:12][CH2:13][CH3:14].C([N:21]([CH2:24]C)CC)C.[OH2:26]>C(Cl)(Cl)Cl>[CH2:11]([O:15][CH2:16][CH2:17][N:18]1[CH:1]=[C:2]([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:21][C:24]1=[O:26])[CH2:12][CH2:13][CH3:14]

Participants

6

Reactant 4

HCID 962WaterHCID 6259Phenacyl bromideHCID 8471TriethylamineHCID 806432-Butoxyethylamine

Product 1

HCID 20229663HCID 20229663, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
0 °C

Procedure

Phenacyl bromide (10 g) in 50 ml of chloroform is added over 20 minutes to a mixture of 2-butoxyethylamine (6 g) and triethylamine (7 g) in 50 ml of chloroform at 0° C. The mixture is stirred for 2 hours. Water (100 ml) is added, the organic layer separated, cooled to 0° C. and glacial acetic acid (5 ml), potassium cyanate (5 g) and methanol (20 ml) are added. The mixture is refluxed for ninety minutes, cooled, washed with saturated sodium bicarbonate solution, dried, and solvent removed to give the title product.

Workup

  1. customthe organic layer separated
  2. additionglacial acetic acid (5 ml), potassium cyanate (5 g) and methanol (20 ml) are added
  3. temperatureThe mixture is refluxed for ninety minutes
  4. temperaturecooled
  5. washwashed with saturated sodium bicarbonate solution
  6. customdried
  7. customsolvent removed

Sources & evidence

ORD record
ord-d9f0ce1fb45749b296eb40ae398c0e8b
Source dataset
uspto-grants-1982_02
Patent number
US04314066

Reaction notes

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