Sulfuric Acid → HCID 178432161, compound

HRID 1076542Notes

Reaction equation

HRID 1076542 reaction equation
[Cl:1][C:2]1[CH:7]=CC(S(CC(C2C=CC=CC=2)=O)=O)=[CH:4][CH:3]=1.S(=O)(=O)(O)O.N=[N+]=[N-].Cl[C:28]1[CH:33]=[CH:32][C:31]([S:34]([CH2:37][C:38]([NH:40][C:41]2[CH:46]=CC=CC=2)=O)(=[NH:36])=[O:35])=[CH:30][CH:29]=1>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:38]2[N:40]=[C:41]([CH3:46])[NH:36][SH:34](=[O:35])([C:31]3[CH:30]=[CH:29][CH:28]=[CH:33][CH:32]=3)[C:37]=2[CH:7]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 24530Hydrazoic acidHCID 13319308HCID 13319308, compoundHCID 86733427HCID 86733427, compound

Product 1

HCID 178432161HCID 178432161, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Following the procedure of (D) but using 83.8 g. (0.30 mole) of 4-chloro-2-(phenylsulfinyl)acetophenone, 500 ml. of chloroform, 250 ml. of concentrated sulfuric acid, and 472 ml. of a 1.4 N chloroform solution of hydrazoic acid, 79.7 g. of a mixture of 4-chloro-2-(phenylsulfonimidoyl)acetanilide and 7-chloro-3-methyl-1-phenyl-1,2,4-benzothiadiazine-1-oxide is obtained. This mixture is stirred and heated under reflux conditions in 450 ml. of 10% sodium hydroxide solution for 3.5 hours. After the mixture is cooled, it is extracted with 500 ml. of chloroform, and the extract is dried and concentrated to give 68.7 g. of a viscous oil. This is extracted with 500 ml. of anhydrous ether. The extract is filtered and cooled in ice. While the extract is cooling in ice, it is treated in a dropwise manner with a slight excess (to pH 4.0) of ethereal hydrogen chloride to give 55.2 g. of product, melting point 217°-219°C after filtration and drying.

Sources & evidence

ORD record
ord-c945b37f23c1410fb56b723d8a35a119
Source dataset
uspto-grants-1976_05
Patent number
US03957769

Reaction notes

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