Sodium Carbonate → N,N'-bis(7-chloro-4-quinazolinyl)-1,9-nonanediamine

HRID 1579239Notes

Reaction equation

HRID 1579239 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([Cl:12])=[CH:9][CH:10]=2)[N:5]=[CH:4][N:3]=1.[NH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][NH2:23].C(=O)([O-])[O-].[Na+].[Na+]>C(O)(C)C>[Cl:12][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([NH:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][NH:23][C:2]3[C:11]4[C:6](=[CH:7][C:8]([Cl:12])=[CH:9][CH:10]=4)[N:5]=[CH:4][N:3]=3)=[N:3][CH:4]=[N:5]2)=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 69534NonamethylenediamineHCID 2418814,7-Dichloroquinazoline

Product 1

HCID 21568196N,N'-bis(7-chloro-4-quinazolinyl)-1,9-nonanediamine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 1.99 g. of 4,7-dichloroquinazoline, 0.79 g. of 1,9-diaminononane, 2.5 g. of sodium carbonate and 25 ml. of isopropanol is stirred at room temperature for 2 hours. The reaction mixture is then diluted with 100 ml. of chloroform, filtered and concentrated in vacuo. The solid residue is crystallized from ethanol to obtain N,N'-bis(7-chloro-4-quinazolinyl)-1,9-nonanediamine, m.p. 190°-192°C. which is readily converted into dimethanesulfonate acid addition salt form which melts at 159°-162°C. on crystallization from ethanol/ether.

Workup

  1. additionA mixture of 1.99 g
  2. additionThe reaction mixture is then diluted with 100 ml
  3. filtrationof chloroform, filtered
  4. concentrationconcentrated in vacuo
  5. customThe solid residue is crystallized from ethanol

Sources & evidence

ORD record
ord-7e942b0b2f4c41b88badd58e8853db51
Source dataset
uspto-grants-1976_01
Patent number
US03931179

Reaction notes

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