Propanoic acid, 2-bromo-2-methyl-, ethyl ester → HCID 14878538, compound

HRID 2073372Notes

Reaction equation

HRID 2073372 reaction equation
[C:1]1([CH2:7][C:8]2[S:12][N:11]=[N:10][C:9]=2[SH:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Na].Br[C:16]([CH3:23])([CH3:22])[C:17]([O:19][CH2:20][CH3:21])=[O:18]>C(O)C>[CH3:22][C:16]([S:13][C:9]1[N:10]=[N:11][S:12][C:8]=1[CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)([CH3:23])[C:17]([O:19][CH2:20][CH3:21])=[O:18]

Participants

5

Reactant 3

HCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 5360545SodiumHCID 14878537HCID 14878537, compound

Product 1

HCID 14878538HCID 14878538, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1.99 g of 5-(phenylmethyl)-1,2,3-thiadiazole-4-thiol, sodium salt in 30 ml of ethanol was stirred overnight with 1.96 g of ethyl 2-bromoisobutyrate and then concentrated in vacuo. The residue was taken up in ether, filtered, and evaporated in vacuo. The oily residue was purified as described in Example 50, giving a yellow oil. Proton nuclear magnetic resonance (δ[ppm], CDCl3) 90MHz: 1.22 (t, 3H); 1.67 (s, 2 CH3 's); 4.12 (q, 2H); 4.31 (s, CH2); 7.30 (6s, SH).

Workup

  1. concentrationconcentrated in vacuo
  2. filtrationfiltered
  3. customevaporated in vacuo
  4. customThe oily residue was purified
  5. customgiving a yellow oil

Sources & evidence

ORD record
ord-316d3083c3a748e39d668fb12475791f
Source dataset
uspto-grants-1990_04
Patent number
US04916237

Reaction notes

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