Acetyl bromide → HCID 20344518, compound

HRID 2049846Notes

Reaction equation

HRID 2049846 reaction equation
[C:1]([Br:4])(=[O:3])[CH3:2].[CH2:5]([NH:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26][OH:27])=[CH:24][CH:23]=1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]>FC(F)(F)C(O)=O.O>[BrH:4].[C:1]([O:27][CH2:26][C:25]1[CH:24]=[CH:23][C:22]([NH:21][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:29][CH:28]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 10482Acetyl bromideHCID 44280121HCID 44280121, compound

Product 1

HCID 20344518HCID 20344518, compound

Reagents, catalysts & solvents 2

HCID 962WaterCatalyst2×HCID 6422Trifluoroacetic acidSolvent

Procedure

Acetyl bromide (0.33 ml.) is added to a solution of p-hexadecylaminobenzyl alcohol (1.0 g.) in trifluoroacetic acid (5 ml.), and the solution is stirred at room temperature for 0.5 hours. Two drops of water are added, and the solution is stirred at room temperature for 0.5 hours. Two drops of water are added, and the solution is evaporated in vacuo. The residue is dissolved in hexanes, and re-evaporated. The residue is treated with anhydrous diethyl ether, and the white solid is collected by filtration, washed with anhydrous diethyl ether, and dried to give 1.01 g. of the product of the Example, m.p. 80°-82° C.

Workup

  1. stirringthe solution is stirred at room temperature for 0.5 hours
  2. customthe solution is evaporated in vacuo
  3. dissolutionThe residue is dissolved in hexanes
  4. customre-evaporated
  5. additionThe residue is treated with anhydrous diethyl ether
  6. filtrationthe white solid is collected by filtration
  7. washwashed with anhydrous diethyl ether
  8. customdried
  9. customto give 1.01 g

Sources & evidence

ORD record
ord-17aed2c7a2ba4c40988a794f61a20c52
Source dataset
uspto-grants-1980_04
Patent number
US04198522

Reaction notes

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