Bromide ion → HCID 178444559, compound

HRID 64773Notes

Reaction equation

HRID 64773 reaction equation
[NH2:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:17])[C:6]=2[C:5]([OH:18])=[CH:4][C:3]=1[SH:19].[Br-].C(=O)([O-])[O-].[Na+].[Na+].CN1[CH2:32][CH2:31][CH2:30][C:29]1=O>>[NH2:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:17])[C:6]=2[C:5]([OH:18])=[CH:4][C:3]=1[S:19][CH2:29][C@H:30]1[CH2:14][CH2:15][C@H:2]([CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])[CH2:32][CH2:31]1

Participants

5

Reactant 4

HCID 259Bromide ionHCID 10340Sodium CarbonateHCID 13387N-methyl-2-pyrrolidoneHCID 4124451-Amino-4-hydroxy-2-mercaptoanthra-9,10-quinone

Product 1

HCID 178444559HCID 178444559, compound

Procedure

To 30 ml of N-methylpyrrolidone, 1 g of 1-amino-2-mercapto-4-hydroxyanthraquinone, 1.2 g of trans-4-n-penthylcyclohexylmethyl bromide and 0.6 g of sodium carbonate were added. The resulting mixture was heated at 120° to 125° C. for 7 hours. After cooling to 60° to 70° C., the mixture was poured on 100 g of ice, followed by separation of the product and washing with water until neutral was obtained. The product thus obtained was dried and purified by column chromatography using silica gel as carrier and chloroform as separating solvent to give 0.7 g of 1-amino-2-(trans-4-n-pentylcyclohexylmethylmercapto)-4-hydroxyanthraquinone having a melting point of 129°-130° C.

Workup

  1. temperatureThe resulting mixture was heated at 120° to 125° C. for 7 hours
  2. temperatureAfter cooling to 60° to 70° C.
  3. customfollowed by separation of the product
  4. washwashing with water
  5. customuntil neutral was obtained
  6. customThe product thus obtained
  7. customwas dried
  8. custompurified by column chromatography
  9. customas separating solvent

Sources & evidence

ORD record
ord-0c6e3d7e605d4cd9b146fe38419ab1e6
Source dataset
uspto-grants-1986_09
Patent number
US04610804

Reaction notes

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