Water → HCID 21841162, compound

HRID 1739451Notes

Reaction equation

HRID 1739451 reaction equation
[Cl:1][C:2]1[C:7]2[S:8][C:9]([C:11](Cl)=[O:12])=[CH:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH2:14]([SH:16])[CH3:15].C(N(CC)CC)C.O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:7]2[S:8][C:9]([C:11](=[O:12])[S:16][CH2:14][CH3:15])=[CH:10][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6343EthanethiolHCID 8471TriethylamineHCID 53925410HCID 53925410, compound

Product 1

HCID 21841162HCID 21841162, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

17.8 g of the 7-chloro-2-benzo[b]thiophenecarboxylic acid chloride prepared in B above, was dissolved in toluene (100 ml), treated with ethanethiol (6.2 ml) followed by dropwise addition of a solution of triethylamine (11.2 ml) in toluene (6 ml) at 15° C., with vigorous stirring, to produce a reaction mixture. The reaction mixture was allowed to come to ambient temperature and then stirred overnight. Water (60 ml) was then added to the reaction mixture and the resultant organic layer was separated. The organic layer was washed with water (50 ml), then with hydrochloric acid (50 ml, 1N), dried (MgSO4), filtered and evaporated, to produce 18,8 g of S-ethyl 7-chloro-2-benzo[b]thiophenecarbothioate.

Workup

  1. customto produce a reaction mixture
  2. customto come to ambient temperature
  3. customthe resultant organic layer was separated
  4. washThe organic layer was washed with water (50 ml)
  5. dry with materialwith hydrochloric acid (50 ml, 1N), dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-1448ddaa0dd046d4b404e12e351515d2
Source dataset
uspto-grants-1999_10
Patent number
US05965749

Reaction notes

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