Isopropanol → HCID 20461260, compound

HRID 543906Notes

Reaction equation

HRID 543906 reaction equation
[O:1]([C:8]([NH:10][C:11](=[S:24])[C:12](=[CH:18]N(CC)CC)[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:25][S:26]([C:29]1[CH:30]=[C:31]([CH:36]=[CH:37][CH:38]=1)[C:32](=[O:35])[CH2:33]Br)(=[O:28])=[O:27].C(O)(C)C>O>[F:25][S:26]([C:29]1[CH:30]=[C:31]([CH:36]=[CH:37][CH:38]=1)[C:32]([C:33]1[S:24][C:11]([NH:10][C:8]([O:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:9])=[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:18]=1)=[O:35])(=[O:28])=[O:27]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 5066471Benzenesulfonyl fluoride, 3-(bromoacetyl)-HCID 54557402HCID 54557402, compound

Product 1

HCID 20461260HCID 20461260, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 130 g of ethyl 2-[[(phenoxycarbonyl)-amino]thioxomethyl]-3-(diethylamino)propenoate (0.37 mole), 104 g of m-fluorosulfonylphenacyl bromide (0.37 mole), and 350 ml of isopropanol was heated to reflux and held one hour. During this time, the reactants dissolved and the product precipitated. The mixture was cooled to 20°-25°, filtered, washed with isopropanol and then water to yield 133 g of white solid, ethyl 5-[3-(fluorosulfonyl)benzoyl]-2-[(phenoxycarbonyl)-amino]-3-thiophenecarboxylate, (75% yield), melting point 161°-163°. Ir: 2.88, 5.72, 5.98, 6.18, 7.12, 8.10, 8.40μ; NMR (CDCl3) δ10.75 (s,1,N-H); 8.4 (m,1); 8.2 (m,2); 7.8 (m,1); 7.7 (s,1, thiophene-proton); 4.4 (q,2); 1.4 (t,3).

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. dissolutionDuring this time, the reactants dissolved
  4. customthe product precipitated
  5. temperatureThe mixture was cooled to 20°-25°
  6. filtrationfiltered
  7. washwashed with isopropanol

Sources & evidence

ORD record
ord-39af3fb6d81441bcb672432b7d559cca
Source dataset
uspto-grants-1984_05
Patent number
US04447624

Reaction notes

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