Hydrochloric Acid → 2-Sulfamoyl-1,3-benzothiazol-5-yl octanoate

HRID 2295755Notes

Reaction equation

HRID 2295755 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([S:10]([NH2:13])(=[O:12])=[O:11])=[N:7][C:6]=2[CH:14]=1.[C:15](Cl)(=[O:23])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].Cl>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[C:15]([O:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([S:10](=[O:12])(=[O:11])[NH2:13])=[N:7][C:6]=2[CH:14]=1)(=[O:23])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8124Octanoyl chlorideHCID 12159529927-14-8

Product 1

HCID 538459422-Sulfamoyl-1,3-benzothiazol-5-yl octanoate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

To a stirred solution of 5-hydroxy-2-benzothiazolesulfonamide (2.3 g., 0.01 mole) and 4-dimethylaminopyridine (100 mg.) in pyridine (15 ml.) is added octanoyl chloride (1.7 ml.) over a period of 5 minutes. The reaction mixture is stirred 11/2 hours, poured into ice water and dilute hydrochloric acid, extracted into ethylacetate, washed with water, dried over magnesium sulfate and chromatographed on 35 g of silica gel (ethyl acetate - hexane 1:1) to give 2-sulfamoyl-5-benzothiazolyl octanoate.

Workup

  1. extractionextracted into ethylacetate
  2. washwashed with water
  3. dry with materialdried over magnesium sulfate
  4. customchromatographed on 35 g of silica gel (ethyl acetate - hexane 1:1)

Sources & evidence

ORD record
ord-d82fe835e1c741f8a0b8ecf7f16dd0df
Source dataset
uspto-grants-1984_01
Patent number
US04426388

Reaction notes

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