Triethylamine → HCID 54199230, compound

HRID 1979655Notes

Reaction equation

[Cl:1][C:2]1[CH:23]=[CH:22][C:5]2[N:6]=[C:7]([O:9][C:10]3[CH:21]=[CH:20][C:13]([O:14][CH:15]([CH3:19])[C:16](Cl)=[O:17])=[CH:12][CH:11]=3)[S:8][C:4]=2[CH:3]=1.S(Cl)(Cl)=[O:25].C(N(CC)CC)C.[CH3:35][O:36][C:37](=[O:40])[CH2:38]S>C1(C)C=CC=CC=1>[CH3:35][O:36][C:37](=[O:40])[CH:38]([C:16](=[O:17])[CH:15]([O:14][C:13]1[CH:20]=[CH:21][C:10]([O:9][C:7]2[S:8][C:4]3[CH:3]=[C:2]([Cl:1])[CH:23]=[CH:22][C:5]=3[N:6]=2)=[CH:11][CH:12]=1)[CH3:19])[OH:25]

Participants

Conditions

Temperature: 25 °C

Procedure

36.8 g or 2-[4-(6-chlorobenzthiazolyloxy)-phenoxy]-propionyl chloride (prepared by reacting 35 g of the free acid with 13.1 g of thionyl chloride in 150 cc of toluene for 8 hours at 80° C.) are added to 150 cc of toluene and a mixture of 12.1 g of triethylamine and 10.6 g of thioglycolic acid methyl ester in 50 cc of toluene is added at 25° to 30° C. The reaction mixture is stirred for a further 2 hours at 50° to 60° C. The mixture is cooled to 25° C. and washed three times with 150 cc of water each. The toluene phase is dried over sodium sulfate, filtered and evaporated to dryness. The residue has completely crystallized after 3 days, yielding 40.5 g (92.7% of theory) of 2-[4-(6-chloro-2-benzthiazolyloxy)-phenoxy]-propionyl-glycolic acid methyl ester. m.p. 104° to 106° C. ##STR13##

Workup

additionis added at 25° to 30° C
washwashed three times with 150 cc of water each
dry with materialThe toluene phase is dried over sodium sulfate
filtrationfiltered
customevaporated to dryness
customThe residue has completely crystallized after 3 days

Sources & evidence

ORD record: ord-18a8f435945b40d49553de400de3f386
Source dataset: uspto-grants-1984_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04482373

Reaction notes

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