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Hydrochloric Acid → HCID 57116472, compound

HRID 544432
Notes
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Reaction equation

HRID 544432 reaction equation
[O:1]([C:8]1[S:9][C:10]([CH2:13][OH:14])=[CH:11][N:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:15][C:16]1([CH3:29])[C@@H:18]([CH:19]=[C:20]2[CH2:24][CH2:23][S:22][C:21]2=[O:25])[C@H:17]1[C:26](Cl)=[O:27].N1C=CC=CC=1.Cl>C1C=CC=CC=1>[CH3:15][C:16]1([CH3:29])[C@@H:18]([CH:19]=[C:20]2[CH2:24][CH2:23][S:22][C:21]2=[O:25])[C@H:17]1[C:26]([O:14][CH2:13][C:10]1[S:9][C:8]([O:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[N:12][CH:11]=1)=[O:27]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 13106154(2-Phenoxy-5-thiazolyl)-methanolHCID 88716027(1R,3S) 2,2-dimethyl-3[(dihydro-2-oxo-3-(2H)-thienylidene)-methyl]-cyclopropane-1-carboxylic acid chloride

Product 1

HCID 57116472HCID 57116472, compoundYield 43.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
20 °C

Procedure

2.1 g of (2-phenoxy-5-thiazolyl)-methanol were added to a solution of 2.44 g of (1R,3S) 2,2-dimethyl-3[(dihydro-2-oxo-3-(2H)-thienylidene)-methyl]-cyclopropane-1-carboxylic acid chloride [described in French Pat. No. 70-21682] in 50 ml of benzene and 3 ml of pyridine were added thereto dropwise at 0° C. The mixture was stirred at 20° C. for 24 hours and was then poured into aqueous 2N hydrochloric acid solution. The decanted organic phase was dried and evaporated to dryness under reduced pressure. The residue was chromatographed over silica gel and was eluted with benzene. The product was crystallized from ethyl acetate to obtain 1.8 g of (2-phenoxy-5-thiazolyl)-methyl (1R,3S) 2,2-dimethyl-3-[(dihydro-2-oxo-3-(2H)-thienylidene)-methyl]-cyclopropane-1-carboxylate.

Workup

  1. customdropwise at 0° C
  2. customThe decanted organic phase was dried
  3. customevaporated to dryness under reduced pressure
  4. customThe residue was chromatographed over silica gel
  5. washwas eluted with benzene
  6. customThe product was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-cc7596375e234cd5808f46107f45c232
Source dataset
uspto-grants-1984_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04450169

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes