Hydrochloric Acid → HCID 57288734, compound

HRID 544436Notes

Reaction equation

HRID 544436 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].Cl>C1C=CC=CC=1.N1C=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]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 13106154(2-Phenoxy-5-thiazolyl)-methanolHCID 88716184HCID 88716184, compound

Product 1

HCID 57288734HCID 57288734, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 1049PyridineSolvent

Conditions

Temperature
20 °C

Procedure

2 g of (2-phenoxy-5-thiazolyl)-methanol were added to a solution of (1R,3R)2,2-dimethyl-3-[(dihydro-2-oxo-3-(2H)-thienylidene)-methyl]-cyclopropane-1-carboxylic acid chloride [described in French Pat. No. 70-21682 published under No. 2.097.244] prepared from 2.2 g of the corresponding acid in 30 ml of benzene and 0.81 ml of pyridine were added thereto at -10° C.The reaction mixture was stirred at 20° C. for 17 hours and was poured into aqueous dilute hydrochloric acid. The decanted aqueous phase was extracted with ether and the combined organic phases were washed with water, dried and evaporated to dryness under reduced pressure. The residuewas chromatographed over silica gel and was eluted with an 8-2 cyclohexane-ethyl acetate mixture to obtain 2.9 g of (2-phenoxy-5-thiazolyl)-methyl (1R,3R) 2,2-dimethyl-3[(dihydro-2-oxo-3-(2H)-thienylidene)-methyl]-cyclopropane-1-carboxylate.

Workup

  1. additionwere added
  2. customat -10° C
  3. extractionThe decanted aqueous phase was extracted with ether
  4. washthe combined organic phases were washed with water
  5. customdried
  6. customevaporated to dryness under reduced pressure
  7. customThe residuewas chromatographed over silica gel
  8. washwas eluted with an 8-2 cyclohexane-ethyl acetate mixture

Sources & evidence

ORD record
ord-003be50959e544faa25abbbabcf9be27
Source dataset
uspto-grants-1984_05
Patent number
US04450169

Reaction notes

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