Hydrochloric Acid → HCID 13236659, compound

HRID 1649384Notes

Reaction equation

HRID 1649384 reaction equation
[OH:1][C:2]1[CH:14]=[CH:13][C:5]2[N:6]=[C:7]([S:9]([NH2:12])(=[O:11])=[O:10])[S:8][C:4]=2[CH:3]=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:14]=[CH:13][C:5]2[N:6]=[C:7]([S:9](=[O:11])(=[O:10])[NH2:12])[S:8][C:4]=2[CH:3]=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 68521296-Hydroxy-1,3-benzothiazole-2-sulfonamide

Product 1

HCID 13236659HCID 13236659, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

To a stirred solution of 6-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 acetatehexane 1:1) to give 0.65 g of 2-sulfamoyl-6-benzothiazolyl octanoate which melts at 114° C. after recrystallization from butyl chloride.

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 acetatehexane 1:1)

Sources & evidence

ORD record
ord-b561c1b9c20e4ab1b1000cd7ebcbe8b4
Source dataset
uspto-grants-1983_11
Patent number
US04416890

Reaction notes

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