Hydrochloric Acid → HCID 13922885, compound

HRID 2232368Notes

Reaction equation

HRID 2232368 reaction equation
[OH:1][C:2]1[CH:14]=[CH:13][C:5]2[S:6][C:7]([S:9](=[O:12])(=[O:11])[NH2:10])=[CH:8][C:4]=2[CH:3]=1.[CH3:15][N:16]([CH3:20])[C:17](Cl)=[O:18].Cl>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[CH3:15][N:16]([C:17]([O:1][C:2]1[CH:14]=[CH:13][C:5]2[S:6][C:7]([S:9]([NH2:10])(=[O:11])=[O:12])=[CH:8][C:4]=2[CH:3]=1)=[O:18])[CH3:20]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6598Dimethylcarbamoyl ChlorideHCID 13922842HCID 13922842, compound

Product 1

HCID 13922885HCID 13922885, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

A solution of 2.3 g (10 mmoles) of 5-hydroxy-2-sulfamoylbenzo[b]thiophene in 50 ml of pyridine was treated with 200 mg of 4-dimethylaminopyridine and finally 2.5 ml (2.9 g, 27 mmoles) of dimethylcarbamyl chloride. The resultant clear solution was stirred at room temperature for 48 hours, when it was poured into a mixture of 200 g of chopped ice and 100 ml of concentrated HCl. The precipitated solid was collected and washed with cold H2O until the washings were neutral. Drying gave 2.25 g (75%) of tan powder which was crystallized from isopropyl alchol to give 1.6 g of product, m.p. 192°-194° C.

Workup

  1. customThe precipitated solid was collected
  2. washwashed with cold H2O until the washings
  3. customDrying

Sources & evidence

ORD record
ord-2840f6a7d37c4510aaa40c5fc8f7d827
Source dataset
uspto-grants-1988_11
Patent number
US04788192

Reaction notes

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