Chlorosulfonic acid → HCID 135622211, compound

HRID 381567Notes

Reaction equation

HRID 381567 reaction equation
[CH3:1][C:2]1[NH:11][C:10](=[O:12])[C:9]2[C:8]3[CH:13]=[CH:14][CH:15]=[CH:16][C:7]=3[CH2:6][CH2:5][C:4]=2[N:3]=1.[Cl:17][S:18](O)(=[O:20])=[O:19]>>[CH3:1][C:2]1[NH:11][C:10](=[O:12])[C:9]2[C:8]3[CH:13]=[C:14]([S:18]([Cl:17])(=[O:20])=[O:19])[CH:15]=[CH:16][C:7]=3[CH2:6][CH2:5][C:4]=2[N:3]=1

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 135838122HCID 135838122, compound

Product 1

HCID 135622211HCID 135622211, compoundYield 41%

Procedure

1,2,5,6-tetrahydro-3-methyl-1-oxobenzo[f]quinazoline (5 g, 0.024 mole) was added to chlorosulfonic acid (50 ml, Aldrich) and stirred for 12 hours at room temperature. The reaction mixture was poured over ice (750 g), and the dark brown solid collected by filtration. The solid was washed with water, suspended in water (500 ml), and the pH of the suspension adjusted to 5.00 by addition of sodium bicarbonate. The suspension was filtered, the product washed with H2O and dried under high vacuum at room temperature to give 1,2,5,6-tetrahydro-3-methyl-oxobenzo[f]quinazolin-9-sulfonyl chloride as a light brown solid (3.054 g, 41%). 1H NMR (DMSO-d6, 300 MHz) δ: 2.60 (s, 3H, CH3); 2.90 (s, 4H, Ar CH2); 7.22 (d, J=9 Hz, 1H, Ar); 7.53 (d, J=9 Hz, 1H, Ar); 8.75 (s, 1H, Ar).

Workup

  1. filtrationthe dark brown solid collected by filtration
  2. washThe solid was washed with water
  3. additionthe pH of the suspension adjusted to 5.00 by addition of sodium bicarbonate
  4. filtrationThe suspension was filtered
  5. washthe product washed with H2O
  6. customdried under high vacuum at room temperature

Sources & evidence

ORD record
ord-b25a8e6b4fe0429fb67fcaea8537c38f
Source dataset
uspto-grants-2001_10
Patent number
US06306865B1

Reaction notes

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