Chloroacetyl chloride → HCID 18377348, compound

HRID 2301092Notes

Reaction equation

C(N(CC)CC)C.[C:8]([O:12][C:13]([NH:15][CH2:16][CH:17]1[NH:22][C:21]2[CH:23]=[CH:24][CH:25]=[CH:26][C:20]=2[S:19][CH2:18]1)=[O:14])([CH3:11])([CH3:10])[CH3:9].[Cl:27][CH2:28][C:29](Cl)=[O:30]>ClCCl>[C:8]([O:12][C:13]([NH:15][CH2:16][CH:17]1[N:22]([C:29](=[O:30])[CH2:28][Cl:27])[C:21]2[CH:23]=[CH:24][CH:25]=[CH:26][C:20]=2[S:19][CH2:18]1)=[O:14])([CH3:11])([CH3:9])[CH3:10]

Participants

Conditions

Temperature: 0 °C

Procedure

A 0.48 ml (3.47 mmol) portion of triethylamine was added to dichloromethane solution (10 ml) containing 0.81 g (2.89 mmol) of 3-(t-butoxycarbonyl)aminomethyl-3,4-dihydro-2H-1,4-benzthiazine and cooled to 0° C. This was mixed with 0.28 ml (3.47 mmol) of chloroacetyl chloride and stirred at room temperature for 3 hours. The reaction solution was poured into ice water and extracted with chloroform. The extract was washed with dilute hydrochloric acid and dried (Na2SO4), and then the solvent was removed by evaporation under a reduced pressure. The thus obtained residue was purified by a silica gel column chromatography (180 cc; elution by ethyl acetate-hexane=1:1) and further recrystallized from ethyl acetate-hexane to obtain 0.64 g of the title compound (62% in yield).

Workup

extractionextracted with chloroform
washThe extract was washed with dilute hydrochloric acid
dry with materialdried (Na2SO4)
customthe solvent was removed by evaporation under a reduced pressure
customThe thus obtained residue was purified by a silica gel column chromatography (180 cc; elution by ethyl acetate-hexane=1:1)
customfurther recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record: ord-9dbfb3f292f3400c9bbe9e23a0302d86
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06498251B1

Reaction notes

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