Acetyl chloride → HCID 24801300, compound

HRID 469808Notes

Reaction equation

HRID 469808 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:17]3[O:16][C:15]([NH:18][C:19]4[CH:24]=[C:23]([O:25][CH3:26])[C:22]([O:27][CH3:28])=[C:21]([O:29][CH3:30])[CH:20]=4)=[N:14][C:13]=3[CH:12]=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[C:31](Cl)(=[O:33])[CH3:32]>N1C=CC=CC=1>[CH3:26][O:25][C:23]1[CH:24]=[C:19]([NH:18][C:15]2[O:16][C:17]3[C:9]([C:6]4[CH:7]=[CH:8][C:3]([CH2:2][NH:1][C:31](=[O:33])[CH3:32])=[CH:4][CH:5]=4)=[CH:10][CH:11]=[CH:12][C:13]=3[N:14]=2)[CH:20]=[C:21]([O:29][CH3:30])[C:22]=1[O:27][CH3:28]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 24801299HCID 24801299, compound

Product 1

HCID 24801300HCID 24801300, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 0.070 g (0.173 mmol) [7-(4-aminomethyl-phenyl)-benzooxazol-2-yl]-(3,4,5-trimethoxy-phenyl)-amine (example 29), 1 ml pyridine and 0.016 g (0.199 mmol) acetyl chloride is stirred for 1.5 h at room temperature. Then the reaction mixture is poured on water and extracted 2× with EtOAc. The combined organic layers are washed with water and 0.1N NaOH solution, dried over MgSO4, filtered and the filtrate is concentrated in vacuo and co-evaporated twice with toluene. The residue is purified by crystallization from dichloromethane/diethyl ether to afford the title compound as a light brown solid. Rt=2.12 min (Waters Symmetry C8, 2.1×50 mm, detection 210-250 nM, 5% to 100% CH3CN in H2O in 2 min+0.05% TFA, flow rate 1.0 ml/min); MS: 448 (M+1)+; m.p. 237-239° C.

Workup

  1. additionThen the reaction mixture is poured on water
  2. extractionextracted 2× with EtOAc
  3. washThe combined organic layers are washed with water and 0.1N NaOH solution
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationthe filtrate is concentrated in vacuo
  7. customThe residue is purified by crystallization from dichloromethane/diethyl ether

Sources & evidence

ORD record
ord-32364e0039a84a14b4338528e9944584
Source dataset
uspto-grants-2014_01
Patent number
US08629168B2

Reaction notes

Loading…