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

HRID 653297Notes

Reaction equation

HRID 653297 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-2c702db0d10f4b29a5bbd671388558b0
Source dataset
uspto-grants-1987_06
Patent number
US04675397

Reaction notes

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