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

HRID 1577643Notes

Reaction equation

HRID 1577643 reaction equation
[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24]([C:26](=[N:33][O:34][CH2:35][C:36]#[N:37])[C:27]([O:29]CC#N)=[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:33][O:34][CH2:35][C:36]#[N:37])[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 53889719HCID 53889719, compound

Product 1

HCID 544542312-(2-Tritylamino-4-thiazolyl)-2-cyanomethoxyimino-acetic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 8.69 g of the product of Step A in 52 ml of dioxane was cooled on an ice bath and 17.1 ml of N sodium hydroxide solution were added thereto dropwise over 20 minutes. Spontaneous heating occured and then 10.5 ml of 2 N hydrochloric acid were added thereto. The dioxane was distilled and only water remained as solvent. 20 ml of water and 30 ml of ether were added thereto and the mixture was stirred for 15 minutes and was vacuum filtered. The crystals were rinsed with water and ether and dried to obtain 4.32 g of the syn isomer of 2-(2-tritylamino-4-thiazolyl)-2-cyanomethoxyimino-acetic acid melting at about 180° C. with decomposition.

Workup

  1. temperaturewas cooled on an ice bath
  2. temperatureSpontaneous heating
  3. distillationThe dioxane was distilled
  4. addition20 ml of water and 30 ml of ether were added
  5. filtrationfiltered
  6. washThe crystals were rinsed with water and ether
  7. customdried

Sources & evidence

ORD record
ord-93ede19f5d4440809a6663aca4060ff4
Source dataset
uspto-grants-1981_09
Patent number
US04288434

Reaction notes

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