Ethanethiol → HCID 21182828, compound

HRID 1387043Notes

Reaction equation

HRID 1387043 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:13][C:12]3[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=3[C:10]=2[C:18]([C:20]2[CH:25]=[CH:24][C:23]([O:26]C)=[C:22]([Br:28])[CH:21]=2)=[O:19])=[CH:5][CH:4]=1.[Al+3].[Cl-].[Cl-].[Cl-].C(S)C>ClCCl>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:13][C:12]3[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=3[C:10]=2[C:18]([C:20]2[CH:25]=[CH:24][C:23]([OH:26])=[C:22]([Br:28])[CH:21]=2)=[O:19])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 6451240Aluminum(III) ChlorideHCID 21182775HCID 21182775, compound

Product 1

HCID 21182828HCID 21182828, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 0° C. solution of 6.5 g (14.3 mmol) of 3-bromo-4-methoxyphenyl 2-(4-methoxyphenyl)benzo[b]thiophen-3-yl ketone in 300 mL of dichloromethane was treated with 15.3 g (115 mmol) of AlCl3, followed by 17 mL (230 mmol) of ethanethiol. The cold bath was removed and the reaction was stirred at ambient temperature for 3.5 h. The reaction mixture was cooled to 0° C. and poured into cold water. The layers were separated and the aqueous layer was extracted with EtOAc (2×150 mL). The combined organic layers were dried over Na2SO4 and evaporated to give 5.9 g (13.9 mmol, 97%) of an oil which crystallized out when mixed with CH2Cl2.

Workup

  1. customThe cold bath was removed
  2. temperatureThe reaction mixture was cooled to 0° C.
  3. additionpoured into cold water
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with EtOAc (2×150 mL)
  6. dry with materialThe combined organic layers were dried over Na2SO4
  7. customevaporated

Sources & evidence

ORD record
ord-62d79862e72e4bc6a97e8874a60a596d
Source dataset
uspto-grants-2001_07
Patent number
US06265575B1

Reaction notes

Loading…