Hydrochloric Acid → 2-(2-Tritylamino-4-thiazolyl)-2-(1-methylethoxyimino)-acetic acid

HRID 354658Notes

Reaction equation

HRID 354658 reaction equation
[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24]([C:26](=[N:32][O:33][CH:34]([CH3:36])[CH3:35])[C:27]([O:29]CC)=[O:28])[N:25]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Cl>O1CCOCC1>[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24]([C:26](=[N:32][O:33][CH:34]([CH3:36])[CH3:35])[C:27]([OH:29])=[O:28])[N:25]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 54071115Ethyl 2-(2-tritylamino-4-thiazolyl)-2-(1-methylethoxyimino)-acetate

Product 1

HCID 542516492-(2-Tritylamino-4-thiazolyl)-2-(1-methylethoxyimino)-acetic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of 6.8 g of the product of Step A, 41 ml of dioxane and 8.15 ml of 2 N sodium hydroxide was heated on a water bath at 55° C. for 2 hours and was then cooled. 9.5 ml of 2 N hydrochloric acid were added to obtain a pH of 2-3 and the dioxane was distilled. Crystallization was effected and water diluted the mixture under stirring. The recovered precipitate was vacuum filtered, rinsed with water, empasted with ether and dried to obtain 5.87 g of the anti isomer of 2-(2-tritylamino-4-thiazolyl)-2-(1-methylethoxyimino)-acetic acid melting at 240° C. (decomp.).

Workup

  1. temperaturewas then cooled
  2. customto obtain a pH of 2-3
  3. distillationthe dioxane was distilled
  4. customCrystallization
  5. additionwater diluted the mixture
  6. filtrationfiltered
  7. washrinsed with water
  8. customdried

Sources & evidence

ORD record
ord-361964a79af4425d8dfdbf9ec633a360
Source dataset
uspto-grants-1983_03
Patent number
US04376203

Reaction notes

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