Chlorosuccinimide → HCID 53242051, compound

HRID 2369372Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][C:10]2[S:14][CH:13]=[N:12][C:11]=2[NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:4][CH:3]=1.[Li]CCCC.[Cl:28]N1C(=O)CCC1=O>C1COCC1.CCCCCC>[Cl:28][C:13]1[S:14][C:10]([C:9]#[C:8][C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[C:11]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:19])([CH3:21])[CH3:20])[N:12]=1

Participants

Conditions

Temperature: -78 °C

Procedure

2.63 g (8.26 mmol) of tert-butyl N-{5-[2-(4-fluorophenyl)ethynyl]-1,3-thiazol-4-yl}carbamate are dissolved in 100 ml of dry THF in a dried Schlenk flask under nitrogen and cooled to −78° C. 11 ml of a 15% solution of n-BuLi in n-hexane are then slowly added dropwise, and the mixture is stirred at −78° C. for 20 min. 1120 mg (8.38 mmol) of N-chlorosuccinimide dissolved in 1 ml of dry THF are subsequently added dropwise, and the mixture is stirred at −78° C. for 15 min, then quenched using 10 ml of n-butanol and warmed to RT. The solvent is removed in vacuo, and the residue is purified directly by chromatography on silica gel (eluent: cyclohexane/ethyl acetate 99/1), giving 2.3 g (6.51 mmol, 78%) of tert-butyl N-{2-chloro-5-[2-(4-fluorophenyl)ethynyl]-1,3-thiazol-4-yl}-carbamate as beige solid from PE; ESI-MS: m/e: 353 ([M+H]+).

Workup

additionare subsequently added dropwise
stirringthe mixture is stirred at −78° C. for 15 min
customquenched
temperaturewarmed to RT
customThe solvent is removed in vacuo
customthe residue is purified directly by chromatography on silica gel (eluent: cyclohexane/ethyl acetate 99/1)

Sources & evidence

ORD record: ord-7f82a398d565454da5187a8c85648fdd
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08703961B2

Reaction notes

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