Water → methyl (2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-propoxyiminoacetate

HRID 2231577Notes

Reaction equation

HRID 2231577 reaction equation
O.[CH3:2][O:3][C:4](=[O:15])[C:5](=[N:10][O:11][CH2:12][CH2:13][CH3:14])[C:6]([CH2:8]Cl)=O.[NH2:16][C:17]([NH2:19])=[S:18].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[CH3:2][O:3][C:4](=[O:15])/[C:5](/[C:6]1[N:16]=[C:17]([NH2:19])[S:18][CH:8]=1)=[N:10]\[O:11][CH2:12][CH2:13][CH3:14]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 2723790ThioureaHCID 542547764-Chloro-2-(n-propoxyimino)acetoacetic acid methyl ester

Product 1

HCID 14230751methyl (2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-propoxyiminoacetate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

To a mixture solution of 20 ml of water and 25 ml of ethanol are added 7.0 g of 4-chloro-2-(n-propoxyimino)acetoacetic acid methyl ester, 2.4 g of thiourea and 4.3 g of sodium acetate(trihydrate). The mixture is stirred for one hour at 40° C. The reaction mixture is, under cooling, adjusted to pH 6.5 with a saturated aqueous solution of potassium carbonate, followed by stirring for 30 minutes. The resulting crystals are collected by filtration, washed with water and isopropyl ether in this order, and dried to yield 2-(2-amino-4-thiazolyl)-(Z)-2-(n-propoxyimino)acetic acid methyl ester as crystals, m.p. 115°-116° C.

Workup

  1. temperatureunder cooling
  2. stirringby stirring for 30 minutes
  3. filtrationThe resulting crystals are collected by filtration
  4. washwashed with water and isopropyl ether in this order
  5. customdried

Sources & evidence

ORD record
ord-f62e8e33fe2647c2824f74065d1c0404
Source dataset
uspto-grants-1988_11
Patent number
US04782147

Reaction notes

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