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Potassium Hydroxide → (2Z)-2-[2-[(2-chloroacetyl)amino]-1,3-thiazol-4-yl]-2-propoxyiminoacetic acid

HRID 2231579
Notes
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Reaction equation

HRID 2231579 reaction equation
C[O:2][C:3](=[O:20])/[C:4](/[C:10]1[N:11]=[C:12]([NH:15][C:16](=[O:19])[CH2:17][Cl:18])[S:13][CH:14]=1)=[N:5]\[O:6][CH2:7][CH2:8][CH3:9].[OH-].[K+]>C(O)C.O>[Cl:18][CH2:17][C:16]([NH:15][C:12]1[S:13][CH:14]=[C:10](/[C:4](=[N:5]/[O:6][CH2:7][CH2:8][CH3:9])/[C:3]([OH:20])=[O:2])[N:11]=1)=[O:19]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 14230755methyl (2Z)-2-[2-[(2-chloroacetyl)amino]-1,3-thiazol-4-yl]-2-propoxyiminoacetate

Product 1

HCID 14230754(2Z)-2-[2-[(2-chloroacetyl)amino]-1,3-thiazol-4-yl]-2-propoxyiminoacetic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 3.2 g of 2-(2-chloroacetamido-4-thiazolyl)-(Z)-2-(n-propoxyimino)acetic acid methyl ester in 50 ml of ethanol is added under ice-cooling and stirring a solution of 2.23 g of potassium hydroxide (85%) in 20 ml of water, and the mixture is stirred for 5 hours at room temperature, followed by concentration under reduced pressure. The concentrate is dissolved in 30 ml of water, and washed twice with 30 ml each portion of ethyl acetate, followed by addition of activated charcoal. The charcoal is removed by filtration and the filtrate is then adjusted to pH 2 with 1N-HCl, and the resulting crystals are collected by filtration, washed with water, hexane and ether in this order to yield 2-(2-chloroacetamido-4-thiazolyl)-(Z)-2-(n-propoxyimino)acetic acid, m.p. 170°-171° C.(decomp.).

Workup

  1. temperaturecooling
  2. concentrationfollowed by concentration under reduced pressure
  3. dissolutionThe concentrate is dissolved in 30 ml of water
  4. washwashed twice with 30 ml each portion of ethyl acetate
  5. additionfollowed by addition of activated charcoal
  6. customThe charcoal is removed by filtration
  7. filtrationthe resulting crystals are collected by filtration
  8. washwashed with water, hexane and ether in this order

Sources & evidence

ORD record
ord-363b241c7a5e404c8219d81393ef27a1
Source dataset
uspto-grants-1988_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04782147

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes