Sulfuric Acid → HCID 13100542, compound

HRID 1577335Notes

Reaction equation

HRID 1577335 reaction equation
S(=O)(=O)(O)O.[NH2:6][C:7]1[C:16]2[C:11](=[C:12]([O:20][CH3:21])[C:13]([O:18][CH3:19])=[C:14]([Cl:17])[CH:15]=2)[N:10]=[C:9]([N:22]2[CH2:27][CH2:26][N:25]([C:28]([O:30][CH2:31][C:32](=[CH2:34])[CH3:33])=[O:29])[CH2:24][CH2:23]2)[N:8]=1.[OH-:35].[Na+]>O>[NH2:6][C:7]1[C:16]2[C:11](=[C:12]([O:20][CH3:21])[C:13]([O:18][CH3:19])=[C:14]([Cl:17])[CH:15]=2)[N:10]=[C:9]([N:22]2[CH2:27][CH2:26][N:25]([C:28]([O:30][CH2:31][C:32]([CH3:33])([OH:35])[CH3:34])=[O:29])[CH2:24][CH2:23]2)[N:8]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 20506467HCID 20506467, compound

Product 1

HCID 13100542HCID 13100542, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred solution of 24 ml. of concentrated sulfuric acid dissolved in an equal volume of water was cooled to 10°-12° C. and 0.015 mole of methallyl 4-(4-amino-6-chloro-7,8-dimethoxyquinazolin-2-yl)piperazine-1-carboxylate is added in small portions with stirring. The addition is carried out at a rate sufficient to keep the reaction temperature below 20° C. The resulting mixture is stirred for 15 minutes at 15°-20° C., then for two hours at 10°-15° C. The reaction mixture is diluted with 150 ml. of ice-water and adjusted to pH 10 with sodium hydroxide while maintaining the temperature below 12° C. After extraction with chloroform, the combined extracts are washed with water and dried over anhydrous sodium sulfate. The solvent is evaporated in vacuo and the residue recrystallized to afford 2-methyl-2-hydroxypropyl 4-(4-amino-6-chloro-7,8-dimethoxyquinazolin-2-yl)piperazine-1-carboxylate.

Workup

  1. temperaturewas cooled to 10°-12° C.
  2. additionThe addition
  3. customthe reaction temperature below 20° C
  4. stirringThe resulting mixture is stirred for 15 minutes at 15°-20° C.
  5. additionThe reaction mixture is diluted with 150 ml
  6. temperaturewhile maintaining the temperature below 12° C
  7. extractionAfter extraction with chloroform
  8. washthe combined extracts are washed with water
  9. dry with materialdried over anhydrous sodium sulfate
  10. customThe solvent is evaporated in vacuo
  11. customthe residue recrystallized

Sources & evidence

ORD record
ord-cd4a6aa691834ad9a6c39780981c2d6d
Source dataset
uspto-grants-1981_09
Patent number
US04287341

Reaction notes

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