Acetyl chloride → HCID 23047238, compound

HRID 2107038Notes

Reaction equation

[H-].[Na+].[O:3]=[C:4]1[NH:9][N:8]=[C:7]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[NH:15][C:14](=[O:19])[C:13]3([CH3:22])[S:20][CH3:21])[CH2:6][S:5]1.[C:23](Cl)(=[O:25])[CH3:24].C(OC(=O)C)C>CN(C=O)C>[C:23]([N:15]1[C:16]2[C:12](=[CH:11][C:10]([C:7]3[CH2:6][S:5][C:4](=[O:3])[NH:9][N:8]=3)=[CH:18][CH:17]=2)[C:13]([CH3:22])([S:20][CH3:21])[C:14]1=[O:19])(=[O:25])[CH3:24]

Participants

Conditions

Temperature: 5 °C

Procedure

0.131 g sodium hydride from a 55% dispersion in mineral oil was added during 0.5 hr to a solution of 0.921 g of 1,3-dihydro-5-(3,6-dihydro-2-oxo-2H-1,3,4-thiadiazin-5-yl)-3-methyl-3-methylthio-2H-indol-2-one (compound of Example 1) in 25 ml DMF at 5° C. The mixture was stirred for 0.5 hr at 5° C. then 0.5 hr at 20° C. and cooled at 5° C. 0.215 ml of acetyl chloride in 1 ml DMF was added dropwise under stirring. The mixture was stirred for 0.5 hr at 5° C. then 1.5 hrs at 20° C. 250 ml ethylacetate was added and the corresponding organic solution was washed with water, dried and evaporated to dryness. The residual oil was purified by chromatography on silica (methylene chloride-ethylacetate: 9/1) to yield 0.4 g of white crystalline compound.

Workup

temperature0.5 hr at 20° C. and cooled at 5° C
stirringunder stirring
stirringThe mixture was stirred for 0.5 hr at 5° C.
custom1.5 hrs
customat 20° C
washthe corresponding organic solution was washed with water
customdried
customevaporated to dryness
customThe residual oil was purified by chromatography on silica (methylene chloride-ethylacetate: 9/1)

Sources & evidence

ORD record: ord-c3970570905641e89a4a3230d5becfe8
Source dataset: uspto-grants-1990_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04933336

Reaction notes

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