Dimethyl Sulfate → HCID 86633699, compound

HRID 502480Notes

Reaction equation

HRID 502480 reaction equation
[NH2:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[C:9]([NH2:17])[CH:10]=[CH:11][CH:12]=3)[C:7](=[O:18])[C:6]=2[C:5]([O:19][CH2:20][CH2:21][N:22]([CH3:24])[CH3:23])=[CH:4][CH:3]=1.N[C:26]1C2C(=O)C3C(=C(N)C=CC=3)C(=O)C=2C(Cl)=CC=1.CNN(NC)CCO.[Na].[CH3:53][O:54][S:55]([O:58]C)(=[O:57])=[O:56]>O.ClC1C=CC=CC=1>[CH3:53][O:54][S:55]([O-:58])(=[O:57])=[O:56].[NH2:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[C:9]([NH2:17])[CH:10]=[CH:11][CH:12]=3)[C:7](=[O:18])[C:6]=2[C:5]([O:19][CH2:20][CH2:21][N+:22]([CH3:26])([CH3:24])[CH3:23])=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 6497Dimethyl SulfateHCID 5360545SodiumHCID 204567661,5-Diamino-4-chloroanthracene-9,10-dioneHCID 22635088HCID 22635088, compoundHCID 68702144HCID 68702144, compound

Product 1

HCID 86633699HCID 86633699, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7964ChlorobenzeneSolvent

Procedure

6.6 parts of 1,5-diamino-4-(2-dimethylamino-ethoxy)-anthraquinone prepared from 1,5-diamino-4-chloro-anthraquinone, N,N-dimethylaminoethanolamine and metallic sodium at 95-120° C. were dispersed in 75 parts of chlorobenzene and treated with 1.4 parts of dimethylsulfate. The reaction mixture was kept for 1½ hours at room temperature. The precipitate was filtered off and stirred with 150 parts of water followed by filtration. The filtrate was evaporated in vacuo yielding 2.5 parts of the dye of formula Ik. The red dye Ik is very good water-soluble. The analytic data are consistent with the assigned structure for dye Ik.

Workup

  1. waitThe reaction mixture was kept for 1½ hours at room temperature
  2. filtrationThe precipitate was filtered off
  3. filtrationfollowed by filtration
  4. customThe filtrate was evaporated in vacuo
  5. customyielding 2.5 parts of the dye of formula Ik

Sources & evidence

ORD record
ord-1e081e530a2740449be7d6ea7a70393f
Source dataset
uspto-grants-2010_08
Patent number
US07776106B2

Reaction notes

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