Hydrochloric Acid → HCID 19359029, compound

HRID 376735Notes

Reaction equation

HRID 376735 reaction equation
C[O:2][C:3]([C:5]1[C:37]([Cl:38])=[CH:36][C:8]2[S:9][C:10]3[CH:15]=[C:14]([NH:16][C:17](=[O:31])[C:18]([C:20]4[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH3:29])[C:21]=4[Cl:30])=[CH2:19])[C:13]([C:32]([O:34]C)=[O:33])=[CH:12][C:11]=3[C:7]=2[CH:6]=1)=[O:4].CC(C)([O-])C.[K+].Cl>CS(C)=O>[Cl:38][C:37]1[C:5]([C:3]([OH:4])=[O:2])=[CH:6][C:7]2[C:11]3[CH:12]=[C:13]([C:32]([OH:34])=[O:33])[C:14]([NH:16][C:17](=[O:31])[C:18]([C:20]4[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH3:29])[C:21]=4[Cl:30])=[CH2:19])=[CH:15][C:10]=3[S:9][C:8]=2[CH:36]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 23665647Potassium tert-butoxideHCID 53850504HCID 53850504, compound

Product 1

HCID 19359029HCID 19359029, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
40 °C

Procedure

To 275 mg of the product of Example 13 was added 4 ml of freshly made 1M potassium t-butoxide in DMSO. The reaction was heated in a 40° C. oil bath and monitored by Mass Spectra for the appearance of product ion. The mixture was poured into 200 ml of cold 1N hydrochloric acid and stirred in the cold for 1 hour. The resulting precipitate was collected, washed with 1N hydrochloric acid and a little water, and dried in vacuo to give the desired product, 3-chloro-7-[2-(2-chloro-3,4-di-methoxyphenyl)-acryloylamino]dibenzothiophene-2,8-dicarboxylic acid.

Workup

  1. customThe resulting precipitate was collected
  2. washwashed with 1N hydrochloric acid
  3. dry with materiala little water, and dried in vacuo

Sources & evidence

ORD record
ord-aed86903ba6947e59ed05cd9e024f349
Source dataset
uspto-grants-2000_02
Patent number
US06022307

Reaction notes

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