Hydrochloric Acid → HCID 13102624, compound

HRID 544426Notes

Reaction equation

[CH3:1][C:2]1([CH3:12])[C@@H:4]([CH:5]=[C:6]([Br:8])[Br:7])[C@H:3]1[C:9](Cl)=[O:10].[CH2:13]([C:20]1[S:21][C:22]([CH2:25][OH:26])=[CH:23][N:24]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.Cl>C1C=CC=CC=1.N1C=CC=CC=1>[CH3:1][C:2]1([CH3:12])[C@@H:4]([CH:5]=[C:6]([Br:8])[Br:7])[C@H:3]1[C:9]([O:26][CH2:25][C:22]1[S:21][C:20]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[N:24][CH:23]=1)=[O:10]

Participants

Conditions

Temperature: 20 °C

Procedure

A solution of 1.26 g of (1R,3R) 2,2-dimethyl-3-(2,2-dibromoethenyl)-cyclopropane-carboxylic acid chloride in 8 ml of benzene was added with stirring at 5° C. to a solution of 0.8 g of (2-benzyl-5-thiazolyl)-methanol in 8 ml of benzene and 0.8 ml of pyridine and the mixture was stirred at 20° C. for 17 hours and was poured into aqueous 2N hydrochloric acid solution with stirring. The decanted organic phase was washed with water and evaporated to dryness under reduced pressure. The residue was chromatographed over silica gel and eluted with a 7-3 hexane-ethyl acetate mixture to obtain 1.41 g of (2-benzyl-5-thiazolyl)-methyl (1R,3R) 2,2-dimethyl-3-[2,2-dibromoethenyl]-cyclopropane-1-carboxylate melting at 66° C. and having a specific rotation of [α]D20 =+9°±1° (c=1% in benzene).

Workup

stirringwith stirring
washThe decanted organic phase was washed with water
customevaporated to dryness under reduced pressure
customThe residue was chromatographed over silica gel
washeluted with a 7-3 hexane-ethyl acetate mixture

Sources & evidence

ORD record: ord-8725822c32fe43988366c1e0f1231756
Source dataset: uspto-grants-1984_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04450169

Reaction notes

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