Acetic Anhydride → HCID 69829045, compound

HRID 1489660Notes

Reaction equation

HRID 1489660 reaction equation
Cl.[NH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][N:11]([CH2:13][CH2:14][CH2:15][O:16][C:17]2[N:21]=[C:20]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[S:19][N:18]=2)[CH3:12])=[CH:5][CH:4]=1.[C:28](OC(=O)C)(=[O:30])[CH3:29].C(=O)([O-])[O-].[Na+].[Na+]>N1C=CC=CC=1>[NH:2]([C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][N:11]([CH2:13][CH2:14][CH2:15][O:16][C:17]2[N:21]=[C:20]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[S:19][N:18]=2)[CH3:12])=[CH:7][CH:8]=1)[C:28]([CH3:29])=[O:30]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 10340Sodium CarbonateHCID 22902364HCID 22902364, compound

Product 1

HCID 69829045HCID 69829045, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

300 mg of 3-{3-[N-(2-(4-aminophenyl)-ethyl)-N-methylamino]-propyloxy}-5-phenyl-1,2,4-thiadiazole (for preparation, see Example 62) were dissolved in 4 ml pyridine. 1 ml of acetic acid anhydride was added to the solution and the reaction mixture was stirred for 2 hours at room temperature. For workup, it was poured over ice and the mixture made alkaline by adding sodium carbonate solution. Then extraction was performed with ethyl acetate, the organic phase was separated, and concentrated to dryness. The crude oily title compound obtained was purified by medium-pressure chromatography over fine-grained silica gel (Lichroprep Si 60®) using 95:5 ethyl acetate/methanol as the eluent. 0.12 g of the title compound were obtained as an oil.

Workup

  1. additionFor workup, it was poured over ice
  2. extractionThen extraction
  3. customthe organic phase was separated
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-e8380bcde76745daa0ab9cb3f160afde
Source dataset
uspto-grants-1997_10
Patent number
US05679699

Reaction notes

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