Aspirin → HCID 178475380, compound

HRID 1606557Notes

Reaction equation

HRID 1606557 reaction equation
[NH:1]=[C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[SH:4](=[O:17])([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[NH:3]1.[C:18]([O:21][C:22]1[C:23](=[CH:27][CH:28]=[CH:29][CH:30]=1)[C:24](O)=[O:25])(=[O:20])[CH3:19].C(N(CC)CC)C>C(Cl)(Cl)Cl>[C:18]([O:21][C:22]1[C:23](=[CH:27][CH:28]=[CH:29][CH:30]=1)[C:24]([N:1]=[C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[SH:4](=[O:17])([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[NH:3]1)=[O:25])(=[O:20])[CH3:19]

Participants

5

Reactant 3

HCID 2244AspirinHCID 8471TriethylamineHCID 178509313HCID 178509313, compound

Product 1

HCID 178475380HCID 178475380, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2.4 g. 3-imino-1-phenyl-3H-1,2-benzisothiazole-1-oxide are boiled for 1 hour with 2 g. acetyl-salicylic acid and 1.32 g. triethylamine in 100 cc. chloroform. After working up in the usual manner, there is obtained 3-(acetylsalicyloylimino)-1-phenyl-3H-1,2-benzisothiazole-1-oxide in the form of colourless crystals which, after recrystallisation from ethyl acetate, melts at 160°C. Structurally, the compounds of this invention are: ##SPC4##Example R1R2 salt melting point (°C)______________________________________ 4 methyl phenoxy -- 138-139 5 phenyl methyl -- 119 6 phenyl ethyl -- 170 7 phenyl iso- -- 122 propyl 8 methyl -- 168-169 9 phenyl -- 13410 methyl -- 17011 methyl methoxy -- 16612 phenyl ethoxy -- 16313 methyl butoxy-2 -- 12514 phenyl phenoxy -- 17315 methyl --O--CH2 --CH2 -- -- 108-190 OCH316 phenyl --CH2 --O--C6H4 -- -- 196 Cl(r)17 phenyl --CH2 --C6H5 -- 12018 methyl --O--C6H11 -- 126-12819 phenyl --C6H4 --O--CO-- -- 160 CH 3 (o)______________________________________

Sources & evidence

ORD record
ord-6cbb93c294a8409b8c2160a48329c938
Source dataset
uspto-grants-1976_04
Patent number
US03953464

Reaction notes

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