Chloroform → HCID 14599947, compound

HRID 1607533Notes

Reaction equation

HRID 1607533 reaction equation
[OH-].[Na+].S[C:4]1[S:5][C:6]2[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=2[N:8]=1.Br[C:14]([CH3:21])([CH3:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16].C(Cl)(Cl)Cl>O.C(O)C.C(O)(C)C.CCCCCC>[CH3:20][C:14]([C:4]1[S:5][C:6]2[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=2[N:8]=1)([CH3:21])[C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

8

Reactant 4

HCID 6212ChloroformHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 14798Sodium HydroxideHCID 178418395HCID 178418395, compound

Product 1

HCID 14599947HCID 14599947, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolvent2×HCID 962WaterSolvent2×HCID 21585144Isopropanol hexaneSolvent

Procedure

3.8 grams of sodium hydroxide was dissolved in 50 ml water. The solution was cooled and to this cooled solution was added 50 ml ethanol. 15 grams of 2-mercaptobenzothiazole was added and the solution diluted with 25 ml ethanol and 25 ml water. Following the addition of 17.5 grams of ethyl 2-bromoisobutyrate the mixture was stirred overnight. The reaction mixture was then concentrated in vacuo and the residue partitioned between ether and water. The ether fraction was washed, (H2O and aqueous Na2CO3) dried (MgSO4), filtered and concentrated in vacuo. This mixture was then partitioned between ether and 10% sodium hydroxide. The ether fraction was washed with 2×25 ml 10% sodium hydroxide and then brine. The ether layer was then dried (MgSO4), filtered, and concentrated to yield a solid which was shown by TLC (CHCl3 and 3% isopropanol/hexane) and 1H NMR to be the titled compound. (b) 2-methyl-2-(2-benzothiazolyl)propionic acid

Workup

  1. temperatureThe solution was cooled and to this cooled solution
  2. concentrationThe reaction mixture was then concentrated in vacuo
  3. customthe residue partitioned between ether and water
  4. washThe ether fraction was washed
  5. dry with material(H2O and aqueous Na2CO3) dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThis mixture was then partitioned between ether and 10% sodium hydroxide
  9. washThe ether fraction was washed with 2×25 ml 10% sodium hydroxide
  10. dry with materialThe ether layer was then dried (MgSO4)
  11. filtrationfiltered
  12. concentrationconcentrated
  13. customto yield a solid which

Sources & evidence

ORD record
ord-2cde3aa328dd4c24a1c6bb62995e8899
Source dataset
uspto-grants-1989_09
Patent number
US04866068

Reaction notes

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