Hydrochloric Acid → 2-[N-(2-Sulfoethyl)carbamoyl]-4-(3,4-methylenedioxybenzyl)amino-6-chloroquinazoline hydrochloride

HRID 1900702Notes

Reaction equation

HRID 1900702 reaction equation
P(C#N)(OCC)(OCC)=O.C(N(CC)CC)C.[C:18]([C:21]1[N:30]=[C:29]([NH:31][CH2:32][C:33]2[CH:38]=[CH:37][C:36]3[O:39][CH2:40][O:41][C:35]=3[CH:34]=2)[C:28]2[C:23](=[CH:24][CH:25]=[C:26]([Cl:42])[CH:27]=2)[N:22]=1)(O)=[O:19].[NH2:43][CH2:44][CH2:45][S:46]([O-:49])(=[O:48])=[O:47].[Na+].Cl>CN(C)C=O.O>[ClH:42].[S:46]([CH2:45][CH2:44][NH:43][C:18]([C:21]1[N:30]=[C:29]([NH:31][CH2:32][C:33]2[CH:38]=[CH:37][C:36]3[O:39][CH2:40][O:41][C:35]=3[CH:34]=2)[C:28]2[C:23](=[CH:24][CH:25]=[C:26]([Cl:42])[CH:27]=2)[N:22]=1)=[O:19])([OH:49])(=[O:48])=[O:47]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 187966952-Carboxy-4-(3,4-methylenedioxybenzyl)amino-6-chloroquinazolineHCID 23666486Sodium Taurate

Product 1

HCID 187967922-[N-(2-Sulfoethyl)carbamoyl]-4-(3,4-methylenedioxybenzyl)amino-6-chloroquinazoline hydrochlorideYield 173.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

0.60 ml (3.8 mmol) of diethyl cyanophosphate and 0.90 ml (6.4 mmol) of triethylamine were dropped, in this order, into a solution of 0.50 g (1.4 mmol) of 2-carboxy-4-(3,4-methylenedioxybenzyl)amino-6-chloroquinazoline and 0.28 g (1.9 mmol) of sodium 2-aminoethanesulfonate in 15 ml of dimethylformamide under cooling with ice and stirring. The obtained mixture was stirred at room temperature for several days, followed by the addition of 10 ml of 1N hydrochloric acid and water. The crystals thus precipitated were recovered by filtration, washed with water and air-dried to give 0.61 g of the title compound.

Workup

  1. temperatureunder cooling with ice
  2. stirringThe obtained mixture was stirred at room temperature for several days
  3. customThe crystals thus precipitated
  4. filtrationwere recovered by filtration
  5. washwashed with water
  6. customair-dried

Sources & evidence

ORD record
ord-99d5e2cf5a4448e482f3cf5d4e7dc297
Source dataset
uspto-grants-1996_11
Patent number
US05576322

Reaction notes

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