3-(2-Chloroethyl)-1,3-oxazolidin-2-one → HCID 13689044, compound

HRID 364187Notes

Reaction equation

[NH2:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH2:11][CH2:12][N:13]([CH2:16][CH3:17])[CH2:14][CH3:15])[N:6]=[C:5]3[C:18]4[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=4[S:20][C:3]=1[C:4]=23.Cl[CH2:26][CH2:27][N:28]1[CH2:32][CH2:31][O:30][C:29]1=[O:33]>C(Cl)(Cl)Cl>[CH2:14]([N:13]([CH2:16][CH3:17])[CH2:12][CH2:11][N:7]1[C:8]2[CH:9]=[CH:10][C:2]([NH:1][CH2:26][CH2:27][N:28]3[CH2:32][CH2:31][O:30][C:29]3=[O:33])=[C:3]3[S:20][C:19]4[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=4[C:5]([C:4]=23)=[N:6]1)[CH3:15]

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 5.8 g 0.017 mol) of 5-amino-N,N-diethyl-2H[1]benzothiopyrano[4,3,2-cd]indazole-2-ethanamine and 5.1 g (0.034 mol) of 3-(2-chloroethyl)-2-oxazolidinone was stirred at 150° C. for two hours, dissolved in 100 ml of CHCl3 and washed twice with 2N NaOH. The solution was dried (MgSO4) and concentrated in vacuo to dryness. The residue was flash chromatographed over silica gel, eluting with a CHCl3 /MeOH (4/1) mixture. The appropriate fractions were combined and concentrated to dryness in vacuo. The residue was treated with 20 ml of acetone and the resulting suspension was treated with 150 ml of Et2O. The resulting precipitate was collected and dried to give 4.9 g of product, mp 90°-94° C.

Workup

washwashed twice with 2N NaOH
dry with materialThe solution was dried (MgSO4)
concentrationconcentrated in vacuo to dryness
customchromatographed over silica gel
washeluting with a CHCl3 /MeOH (4/1) mixture
concentrationconcentrated to dryness in vacuo
additionThe residue was treated with 20 ml of acetone
additionthe resulting suspension was treated with 150 ml of Et2O
customThe resulting precipitate was collected
customdried

Sources & evidence

ORD record: ord-59084415c0ba4959b94975e188c07e95
Source dataset: uspto-grants-1986_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04604390

Reaction notes

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