Acetic Anhydride → HCID 20300066, compound

HRID 1733555Notes

Reaction equation

HRID 1733555 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]3[N:15]([CH:16]=2)[CH:14]=[CH:13][S:12]3)=[CH:5][CH:4]=1.[CH2:17]([N:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21]([C:28]([C:30]2[C:35]([C:36]([OH:38])=[O:37])=[CH:34][CH:33]=[CH:32][N:31]=2)=O)=[C:20]1[CH3:39])[CH3:18].C(OC(=O)C)(=O)C.[OH-].[NH4+]>O>[CH2:17]([N:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21]([C:28]2([C:16]3[N:15]4[C:11]([S:12][CH:13]=[CH:14]4)=[N:10][C:9]=3[C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[C:30]3=[N:31][CH:32]=[CH:33][CH:34]=[C:35]3[C:36](=[O:37])[O:38]2)=[C:20]1[CH3:39])[CH3:18]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 14923Ammonium HydroxideHCID 1123443-Pyridinecarboxylic acid, 2-((1-ethyl-2-methyl-1H-indol-3-yl)carbonyl)-HCID 369507NSC641287

Product 1

HCID 20300066HCID 20300066, compoundYield 123.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.92 gram of 6-p-methoxy phenylimidazo[2,1-b]thiazole, 0.69 gram of (1-ethyl-2-methylindol-3-yl)(3-carboxypyridin-2-yl)ketone and 20 ml. of acetic anhydride was stirred 2.5 hours at 50° C. The reaction solution was poured into 250 ml. of water and adjusted to pH 9.8 with ammonium hydroxide. After one hour stirring the solid material was filtered and washed with water to give 1.44 grams (95%) of desired product, mp. 115°-118° C. The infrared spectrum showed a strong 1770 cm-1 lactone carbonyl peak. A solution of the product on silica gel produced a purple color.

Workup

  1. additionThe reaction solution was poured into 250 ml
  2. filtrationwas filtered
  3. washwashed with water

Sources & evidence

ORD record
ord-4b1c835a998f463aafd6d4f2241a8553
Source dataset
uspto-grants-1980_12
Patent number
US04242513

Reaction notes

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