Ethyl chloroformate → HCID 16069189, compound

HRID 1666705Notes

Reaction equation

[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[O:10][CH2:11][C:12]([OH:14])=O.ClC(OCC)=O.[Cl:21][C:22]1[CH:23]=[C:24]([CH:32]=[CH:33][C:34]=1[Cl:35])[CH2:25][N:26]([CH3:31])[CH2:27][CH2:28][CH2:29][NH2:30]>C(Cl)(Cl)Cl>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[O:10][CH2:11][C:12]([NH:30][CH2:29][CH2:28][CH2:27][N:26]([CH2:25][C:24]1[CH:32]=[CH:33][C:34]([Cl:35])=[C:22]([Cl:21])[CH:23]=1)[CH3:31])=[O:14]

Participants

Conditions

Temperature: -15 °C

Procedure

To the solution of 54 mg (0.28 mmol) (1,3-benzoxazol-2-yloxy)acetic acid in 3 ml chloroform 28 mg (0.28 mmol) 4-methylmorpholine is added. The mixture is cooled to −15° C., 30 mg (0.28 mmol) ethyl chloroformate is dropped to it and the mixture is stirred under cooling for 15 minutes. Then the solution of 83 mg (0.34 mmol) N-(3,4-dichlorobenzyl)-N-(methyl)propane-1,3-diamine in 2 ml chloroform is added and the reaction mixture is stirred for 30 min under cooling and 1 hour at room temperature. The chloroform solution is extracted with 2×10 ml water, the organic phase is dried over sodium sulfate and evaporated in vacuum to obtain 50 mg title compound as an oil. LC/MS[MH+]=422 (C20H21Cl2N3O3 422.31).

Workup

temperatureunder cooling for 15 minutes
stirringthe reaction mixture is stirred for 30 min
temperatureunder cooling and 1 hour at room temperature
extractionThe chloroform solution is extracted with 2×10 ml water
dry with materialthe organic phase is dried over sodium sulfate
customevaporated in vacuum

Sources & evidence

ORD record: ord-08629145923d40dea0292ab2336defc8
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08044078B2

Reaction notes

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