Methanesulfonyl chloride → HCID 131714589, compound

HRID 483143Notes

Reaction equation

HRID 483143 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11][C:10](=[O:18])[NH:9]2)[CH:5]=[CH:6][CH:7]=1.[S:19](Cl)([CH3:22])(=[O:21])=[O:20]>ClCCl.C(N(CC)CC)C>[OH2:18].[CH3:22][S:19]([NH:1][C:2]1[CH:3]=[C:4]([CH:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11][C:10](=[O:18])[NH:9]2)[CH:5]=[CH:6][CH:7]=1)(=[O:21])=[O:20].[CH3:22][S:19]([NH:1][C:2]1[CH:3]=[C:4]([CH:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11][C:10](=[O:18])[NH:9]2)[CH:5]=[CH:6][CH:7]=1)(=[O:21])=[O:20]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 202425531-(3-Aminophenyl)-1,4-dihydroisoquinol-3-one

Product 1

HCID 131714589HCID 131714589, compoundYield 48.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

A solution of 1-(3-aminophenyl)-1,4-dihydroisoquinol-3-one (8.0 g) in dichloromethane (500 ml) and triethylamine (50 ml) was treated dropwise, at room temperature, with a solution of mesyl chloride (9.7 g) in dichloromethane (20 ml). After stirring for 3 h, the resulting precipitate (m.p. 251°-253° C.) was collected, washed with dichloromethane, water, and air dried. The product was stirred with a mixture of 10% aqueous sodium hydroxide (200 ml) and methanol (20 ml) at 50° C. for 1 h. The mixture was filtered and the filtrate was evaporated to one third volume in vacuo. It was acidified with dilute hydrochloric acid, and the resulting precipitate was collected and washed with water. Recrystallisation from methanol-ether afforded the title compound (3.55 g)

Workup

  1. customthe resulting precipitate (m.p. 251°-253° C.) was collected
  2. washwashed with dichloromethane, water, and air
  3. customdried
  4. stirringThe product was stirred with a mixture of 10% aqueous sodium hydroxide (200 ml) and methanol (20 ml) at 50° C. for 1 h
  5. filtrationThe mixture was filtered
  6. customthe filtrate was evaporated to one third volume in vacuo
  7. customthe resulting precipitate was collected
  8. washwashed with water
  9. customRecrystallisation from methanol-ether

Sources & evidence

ORD record
ord-4794dafb8d5f4a8babe4dcf675b28e02
Source dataset
uspto-grants-1986_03
Patent number
US04578393

Reaction notes

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