Water → HCID 88627667, compound

HRID 1194907Notes

Reaction equation

HRID 1194907 reaction equation
[Cl:1][C:2]([Cl:38])=[CH:3][CH2:4][O:5]/[N:6]=[C:7](/[C:13]1[N:14]=[C:15]([NH:18]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[S:16][CH:17]=1)\[C:8]([O:10][CH2:11][CH3:12])=[O:9].O>C(O)=O>[NH2:18][C:15]1[S:16][CH:17]=[C:13](/[C:7](=[N:6]/[O:5][CH2:4][CH:3]=[C:2]([Cl:38])[Cl:1])/[C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:14]=1

Participants

4

Reactant 2

HCID 962Water2×HCID 140352838HCID 140352838, compound

Product 1

HCID 88627667HCID 88627667, compoundYield 84.3%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent2×

Procedure

Ethyl (Z)-2-(3,3-dichloroprop-2-en-1-yloxyimino)-2-(2-triphenylmethylaminothiazol-4-yl)acetate (622 mg, 1.09 mmol) was dissolved in 98% formic acid (5 ml) and treated with water (1.5 ml). After stirring for 2 h the formic acid and water were removed under reduced pressure. Toluene was added and the process repeated. The residue was chromatographed on silica-gel eluting with ethyl acetate/hexane mixtures to give the title compound (298 mg, 84%) m.p. 135°-136°; [Found C, 37.25; H, 3.46; N, 13.12. C10H11Cl2N3O3S requires C, 37.05; H, 3.42; N, 12.96%]. νmax (CH2Cl2) 3475, 3380, 3110, 1735, 1605, 1530, 1375, 1180, and 1025 cm-1 ; δH (60 MHz, CDCl3) 1.30 (3H, t, J ca 7 Hz), 4.37 (2H, q, J ca 7 Hz), 4.72 (2H, d, J ca 6.5 Hz), 5.83 (2H, broad s), 6.1 (1H, t, J ca 6.5 Hz), and 6.66 (1H, s).

Workup

  1. customwere removed under reduced pressure
  2. additionToluene was added
  3. customThe residue was chromatographed on silica-gel
  4. washeluting with ethyl acetate/hexane

Sources & evidence

ORD record
ord-5282dab60cc048758ea80fc74e5b24e6
Source dataset
uspto-grants-1989_03
Patent number
US04816452

Reaction notes

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