Sodium hydride → 2-(2-Chloro-5-thiazolyl)methoxymethyl-8-phenethyl-1,4-dioxa-8-azaspiro[4,5]decane

HRID 77338

Reaction equation

[H-].[Na+].[OH:3][CH2:4][CH:5]1[CH2:9][O:8][C:7]2([CH2:14][CH2:13][N:12]([CH2:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:11][CH2:10]2)[O:6]1.[Cl:23][C:24]1[S:25][C:26]([CH2:29]Cl)=[CH:27][N:28]=1>C1(C)C=CC=CC=1>[Cl:23][C:24]1[S:25][C:26]([CH2:29][O:3][CH2:4][CH:5]2[CH2:9][O:8][C:7]3([CH2:10][CH2:11][N:12]([CH2:15][CH2:16][C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH2:13][CH2:14]3)[O:6]2)=[CH:27][N:28]=1

Participants

Conditions

Temperature: 28 °C

Procedure

To 8.64 g (0.36 mole) of sodium hydride in toluene (250 ml) was added 2-hydroxymethyl-8-phenethyl-1,4-dioxa-8-azaspiro[4,5]decane (compound 1.50 gm, 0.18 mole) in toluene (350 ml) with stirring at 28° C. The phase transfer catalyst tetrabutylammonium bromide TBAB 2 gm was added and 31 gm of 2-chloro-5-chloromethylthiazole in toluene (225 ml) was then added drop wise at 10° C. and the reaction mixture was refluxed for 15 hrs. The reaction mixture was washed with water and the product was extracted with methylene chloride 100 ml. The solvent was distilled off to get thick dark colored liquid. The yield of the product was 85%.

Workup

temperaturethe reaction mixture was refluxed for 15 hrs
washThe reaction mixture was washed with water
extractionthe product was extracted with methylene chloride 100 ml
distillationThe solvent was distilled off
customto get thick dark colored liquid

Sources & evidence

ORD record: ord-2cfa75405cf349088974236ec659b8bc
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841296B2

Linked notes

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