Trityl chloride → Ethyl 2-(2-tritylamino-4-thiazolyl)-2-hydroxyimino-acetate hydrochloride

HRID 2049170Notes

Reaction equation

[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:13][OH:14])[C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:6]=1.C(N(CC)CC)C.[C:22]([Cl:41])([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C)C=O>[ClH:41].[C:22]([NH:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:13][OH:14])[C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:6]=1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

Conditions

Temperature: -35 °C

Procedure

A mixture of 43.2 g of the product of Step A in 120 ml of dry dimethylformamide was cooled to -35° C. and after the addition of 32 ml of triethylamine, 60 g of trityl chloride were added thereto in fractions over 30 minutes. The temperature was allowed to increase during which total dissolution occurred and the mixture was heated at 30° C. for one hour and was then poured into 1.2 liters of ice water containing 40 ml of 22° Be hydrochloric acid. The mixture was stirred in an ice bath and was then vacuum filtered. The recovered product was rinsed with N hydrochloric acid and was empasted with ether to obtain 69.3 g of the syn isomer of ethyl 2-(2-tritylamino-4-thiazolyl)-2-hydroxyimino-acetate HCl.

Workup

additionwere added
temperatureto increase during which total dissolution
temperaturethe mixture was heated at 30° C. for one hour
filtrationvacuum filtered
washThe recovered product was rinsed with N hydrochloric acid

Sources & evidence

ORD record: ord-8611b04f611b41938cd4842f5be72151
Source dataset: uspto-grants-1980_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04196205

Reaction notes

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