Hydrochloric Acid → 2-Sulfamoyl-6-benzothiazolyl dodecanoate

HRID 1649385Notes

Reaction equation

HRID 1649385 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(N(CC)CC)C.[C:22](Cl)(=[O:34])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33].Cl>CN(C)C1C=CN=CC=1.CN(C)C=O>[C:22]([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:34])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8166Dodecanoyl chlorideHCID 8471TriethylamineHCID 68521296-Hydroxy-1,3-benzothiazole-2-sulfonamide

Product 1

HCID 132366612-Sulfamoyl-6-benzothiazolyl dodecanoate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 6-hydroxy-2-benzothiazolesulfonamide (6.9 g., 0.03 mole), triethylamine (4.2 ml., 0.03 mole) and 4-dimethylaminopyridine (100 mg.) in dimethylformamide (30 ml.) is added lauroyl chloride (7 ml.) during a 1/2 hour period. The reaction mixture is stirred for 2 hours at room temperature, poured into ice water and hydrochloric acid, extracted into ether, washed with water, ammonium hydroxide (3 ml. diluted with water) dilute hydrochloric acid and dried over magnesium sulfate. The ether is evaporated at reduced pressure to give 2.2 g of 2-sulfamoyl-6-benzothiazolyl dodecanoate which melts at 112°-114° C. after recrystallization from butyl chloride.

Workup

  1. extractionextracted into ether
  2. washwashed with water, ammonium hydroxide (3 ml. diluted with water) dilute hydrochloric acid
  3. dry with materialdried over magnesium sulfate
  4. customThe ether is evaporated at reduced pressure

Sources & evidence

ORD record
ord-c0399c2f39794e11a04ed97c020344a9
Source dataset
uspto-grants-1983_11
Patent number
US04416890

Reaction notes

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