Acetaldehyde → 4-ethylamino-N-(2,1,3-benzothiadiazol-5-yl)-1-benzenesulfonamide

HRID 1624

Reaction equation

HRID 1624 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:20]=[CH:19][C:15]3=[N:16][S:17][N:18]=[C:14]3[CH:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH:21](=O)[CH3:22].C([BH3-])#N.[Na+].Cl>CO.[Ti](Cl)(Cl)(Cl)Cl>[CH2:21]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:20]=[CH:19][C:15]3=[N:16][S:17][N:18]=[C:14]3[CH:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1)[CH3:22]

Participants

7

Reactant 4

HCID 177AcetaldehydeHCID 313Hydrochloric AcidHCID 5003444Sodium cyanoborohydrideHCID 196918994-amino-N-(2,1,3-benzothiadiazol-5-yl)-1-benzenesulfonamide

Product 1

HCID 196919084-ethylamino-N-(2,1,3-benzothiadiazol-5-yl)-1-benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 887MethanolSolvent

Procedure

A solution of 6 g of 4-amino-N-(2,1,3-benzothiadiazol-5-yl)-1-benzenesulfonamide and 0.5 g of titanium tetrachloride in 100 ml of methanol is treated with 1 ml of freshly distilled acetaldehyde. 4 g of sodium cyanoborohydride are then added thereto and the mixture is stirred for 30 hours. Cold half-concentrated hydrochloric acid is added thereto, the mixture is worked up in the customary manner and 4-ethylamino-N-(2,1,3-benzothiadiazol-5-yl)-1-benzenesulfonamide is obtained.

Sources & evidence

ORD record
ord-a7fa891adf0d455598641c30d6e12a91
Source dataset
uspto-grants-1998_03
Patent number
US05726194

Linked notes

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