Sulfuric Acid → HCID 20553463, compound
Reaction equation
O.[ClH:2].[ClH:3].Cl.[CH2:5]([N:7]([CH2:33][CH3:34])[CH2:8][CH2:9][O:10][C:11]1[CH:12]=[CH:13][C:14]2[C:23]([CH:24]=1)=[N:22][C:21]1[C:16](=[CH:17][CH:18]=[C:19]([O:25][CH2:26][CH2:27][N:28]([CH2:31][CH3:32])[CH2:29][CH3:30])[CH:20]=1)[CH:15]=2)[CH3:6].S(=O)(=O)(O)O.ClN1C(=O)CCC1=O>>[CH2:29]([N:28]([CH2:31][CH3:32])[CH2:27][CH2:26][O:25][C:19]1[CH:18]=[CH:17][C:16]2[C:21]([C:20]=1[Cl:2])=[N:22][C:23]1[C:14](=[CH:13][CH:12]=[C:11]([O:10][CH2:9][CH2:8][N:7]([CH2:5][CH3:6])[CH2:33][CH3:34])[C:24]=1[Cl:3])[CH:15]=2)[CH3:30]Participants
4
Procedure
A 2.148 g. portion of 3,6-bis(2-diethylaminoethoxy)acridine trihydrochloride monohydrate is dissolved in 8 ml. of concentrated sulfuric acid. This solution is cooled in an ice bath and 1.175 g. of N-chlorosuccinimide are added. The procedure of Example 3 is followed giving 1.5 g. of a reddish brown crude product. This product is dissolved in 100 ml. of dichloromethane and filtered through a 2 inch×21/2 inch bed of alumina. The filter bed is washed with one liter of dichloromethane, then one liter of ethyl acetate. The filtrates are combined, concentrated in vacuo and the residue is crystallized from 10 ml. of hexane giving 1.067 g. of the desired product as yellow crystals, m.p. 83°-84° C.
Workup
- temperatureThis solution is cooled in an ice bath
- customThe procedure of Example 3 is followed giving 1.5 g
- dissolutionThis product is dissolved in 100 ml
- filtrationof dichloromethane and filtered through a 2 inch×21/2 inch bed of alumina
- washThe filter bed is washed with one liter of dichloromethane
- concentrationconcentrated in vacuo
- customthe residue is crystallized from 10 ml
Sources & evidence
- ORD record
- ord-4523210102c143c498b85512aa523e9e
- Source dataset
- uspto-grants-1982_02
- Patent number
- US04314061
Reaction notes
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