Ethanethiol → HCID 21306325, compound

HRID 2085065Notes

Reaction equation

HRID 2085065 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([S:9]([NH:12][CH:13]([CH3:20])[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])(=[O:11])=[O:10])[CH:6]=[CH:7][CH:8]=1.C(S)C.[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[C:5]([S:9]([NH:12][CH:13]([CH3:20])[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])(=[O:11])=[O:10])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 6451240Aluminum(III) ChlorideHCID 21306331HCID 21306331, compound

Product 1

HCID 21306325HCID 21306325, compoundYield 94.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of β-[[(3-methoxypheyl)sulfonyl]amino]-butanoic acid, ethyl ester (7.8 g, 25.7 mmol) and ethanethiol (8 g, 0.13 mol) in methylenechloride (200 ml) was cooled in ice-bath. Aluminum chloride (17.2 g, 0.13 mol) was added to above solution. The reaction mixture was stirred at room temperature for 4 hours. The reaction mixture was quenched with 3N HCl (200 ml). Organic layer was separated. Aqueous layer was extracted with methylene chloride (2×100 ml). Combined organic solution was concentrated and dried to give the title compound (7 g, 94%). The material was used for the next reaction without further purification. 1H NMR (300 MHz, CD3OD) δ 1.06 (d, 3H, J=6.73 Hz), 1.23 (t, 3H, J=7.11 Hz), 2.31-2.49 (m, 2H), 3.66-3.74 (m, 1H), 4.01-4.16 (m, 2H), 7.00-7.04 (m, 1H), 7.2-7.41 (m, 3H).

Workup

  1. temperaturewas cooled in ice-bath
  2. customThe reaction mixture was quenched with 3N HCl (200 ml)
  3. customOrganic layer was separated
  4. extractionAqueous layer was extracted with methylene chloride (2×100 ml)
  5. concentrationCombined organic solution was concentrated
  6. customdried

Sources & evidence

ORD record
ord-09ad7393004244a2966404c9d00a5542
Source dataset
uspto-grants-2004_04
Patent number
US06720315B2

Reaction notes

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