Triethylamine → HCID 70584365, compound

HRID 1390805Notes

Reaction equation

HRID 1390805 reaction equation
[NH2:1][C@H:2]1[C:5](=[O:6])[N:4]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][C:9]=2[O:16][CH3:17])[C@H:3]1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH:24]1[O:28][CH2:27][CH2:26][O:25]1.C(N(CC)CC)C.[O:36]([CH2:43][C:44](Cl)=[O:45])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>C(OCC)(=O)C>[CH3:17][O:16][C:9]1[CH:10]=[C:11]([O:14][CH3:15])[CH:12]=[CH:13][C:8]=1[CH2:7][N:4]1[C:5](=[O:6])[C@H:2]([NH:1][C:44](=[O:45])[CH2:43][O:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C@@H:3]1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH:24]1[O:28][CH2:27][CH2:26][O:25]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 69703Phenoxyacetyl chlorideHCID 70584361HCID 70584361, compound

Product 1

HCID 70584365HCID 70584365, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The amino compound from Example 3 (4.22 g, 11 mmol) was dissolved in ethyl acetate (60 ml) and cooled in an ice-alcohol bath. Triethylamine (1.67 g, 16.5 mmol) was added, followed by the dropwise addition of phenoxyacetyl chloride (2.06 g, 12.1 mmol) over a period of 5 minutes. The reaction was stirred for 45 minutes with cooling and then filtered. The filtrate was washed with 5% NaHCO3 and brine. The dried filtrate was evaporated to give the title product; 2.0 g. The product was recrystallized from ethyl acetate-ether; 1.02 g, mp 137-138°. The solid which was filtered from the reaction solution was stirred with hot ethyl acetate (100 ml) and filtered. The filtrate was treated with ether (200 ml) and cooled to give additional product; 3.91 g, mp 138-139°.

Workup

  1. temperaturecooled in an ice-alcohol bath
  2. temperaturewith cooling
  3. filtrationfiltered
  4. washThe filtrate was washed with 5% NaHCO3 and brine
  5. customThe dried filtrate was evaporated

Sources & evidence

ORD record
ord-96b1a81381be4b79bf9b02f4e12524d6
Source dataset
uspto-grants-1979_02
Patent number
US04140688

Reaction notes

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