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Triethylamine → HCID 54199230, compound

HRID 1979655
Notes
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Reaction equation

HRID 1979655 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 16907Methyl ThioglycolateHCID 24386Thionyl ChlorideHCID 134885362-{4-[(6-Chloro-1,3-benzothiazol-2-yl)oxy]phenoxy}propanoyl chloride

Product 1

HCID 54199230HCID 54199230, compoundYield 92.7%

Reagents, catalysts & solvents 1

HCID 1140
Toluene
Solvent
3×

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

  1. additionis added at 25° to 30° C
  2. washwashed three times with 150 cc of water each
  3. dry with materialThe toluene phase is dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness
  6. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes