Hydrochloric Acid → HCID 112438, compound

HRID 569672Notes

Reaction equation

HRID 569672 reaction equation
[CH3:1][N:2]([CH3:22])[C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[C:18]3[C:13](=[CH:14][C:15]([N:19]([CH3:21])[CH3:20])=[CH:16][CH:17]=3)[C:11](=[O:12])[O:10]2)=[CH:5][CH:4]=1.[CH3:23][N:24]([CH3:34])[C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([N:31]([CH3:33])[CH3:32])[CH:26]=1.[OH-].[K+].Cl>O>[CH3:32][N:31]([CH3:33])[C:27]1[CH:26]=[C:25]([N:24]([CH3:34])[CH3:23])[CH:30]=[CH:29][C:28]=1[CH:9]([C:18]1[CH:17]=[CH:16][C:15]([N:19]([CH3:21])[CH3:20])=[CH:14][C:13]=1[C:11]([OH:10])=[O:12])[C:6]1[CH:7]=[CH:8][C:3]([N:2]([CH3:22])[CH3:1])=[CH:4][CH:5]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 897151,3-Benzenediamine, N1,N1,N3,N3-tetramethyl-HCID 936931(3H)-Isobenzofuranone, 6-(dimethylamino)-3-[4-(dimethylamino)phenyl]-

Product 1

HCID 112438HCID 112438, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 6.0 g of 3-(4-dimethylaminophenyl)-6-dimethylaminophthalide prepared as described in part A above, 100 ml of water, 3.5 g of N,N,N',N'-tetramethyl-m-phenylenediamine and 1.8 g of flake potassium hydroxide was heated at reflux with stirring for a period of approximately eighteen hours and then allowed to cool to room temperature. The resultant solution was made slightly acidic by the addition of ten percent aqueous hydrochloric acid causing a cream-colored solid to precipitate. The solid was collected by filtration, washed with water and air dried at 40° C. to obtain 2-[2,4,4'-tris(dimethylamino)benzhydryl]-5-dimethylaminobenzoic acid (Formula III: R=CH3 ; X=H; Y=4-(CH3)2NC6H4 ; Z=2,4-[(CH3)2N]2C6H3) as a slightly sticky, cream-colored solid melting over the range 119°-121° C.

Workup

  1. customprepared
  2. temperaturewas heated
  3. temperatureat reflux
  4. customto precipitate
  5. filtrationThe solid was collected by filtration
  6. washwashed with water and air
  7. customdried at 40° C.

Sources & evidence

ORD record
ord-9fe5709ab00f4603aa08567490ac11e6
Source dataset
uspto-grants-1988_03
Patent number
US04732991

Reaction notes

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