Hydrochloric Acid → Ethyl benzo-1,2,3-thiadiazole-7-carboximidate hydrochloride

HRID 1769966Notes

Reaction equation

HRID 1769966 reaction equation
[C:1]([C:3]1[C:11]2[S:10][N:9]=[N:8][C:7]=2[CH:6]=[CH:5][CH:4]=1)#[N:2].[ClH:12].[CH2:13]([O:15]CC)[CH3:14]>C(O)C.O1CCCC1>[ClH:12].[S:10]1[C:11]2[C:3]([C:1](=[NH:2])[O:15][CH2:13][CH3:14])=[CH:4][CH:5]=[CH:6][C:7]=2[N:8]=[N:9]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 22182879Acibenzolar Acid Impurity 21

Product 1

HCID 20096457Ethyl benzo-1,2,3-thiadiazole-7-carboximidate hydrochloride

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

7.2 g of 7-cyanobenzo-1,2,3-thiadiazole are dissolved at 45° C. in 60 ml of absolute ethanol and 20 ml of tetrahydrofuran, and the solution is cooled to 0° C. and saturated with gaseous hydrochloric acid in the course of 1 hour at 0° C. to 15° C., with the exclusion of moisture. The reaction mixture is then stored for 24 hours in the refrigerator, treated with 70 ml of absolute diethyl ether and allowed to stand for another 4 days in the refrigerator. The solid is then filtered off, washed with diethyl ether and dried. This gives 9.4 g of compound 5.2 in the form of beige crystals of m.p. 270°-272° C.

Workup

  1. waitto stand for another 4 days in the refrigerator
  2. filtrationThe solid is then filtered off
  3. washwashed with diethyl ether
  4. customdried

Sources & evidence

ORD record
ord-f50c70fbf4524d6691d0695b5ea79fac
Source dataset
uspto-grants-1995_01
Patent number
US05384321

Reaction notes

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