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

HRID 2295756Notes

Reaction equation

HRID 2295756 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(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: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: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 12159529927-14-8

Product 1

HCID 537879332-Sulfamoyl-1,3-benzothiazol-5-yl dodecanoate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 5-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-sulfamoyl-5-benzothiazolyl dodecanoate.

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-35ec615e6f684d299c12fef01b4f4dab
Source dataset
uspto-grants-1984_01
Patent number
US04426388

Reaction notes

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