Bromine → HCID 13340370, compound

HRID 2052471Notes

Reaction equation

HRID 2052471 reaction equation
[NH2:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[CH2:4][NH:5][C@H:6]([C:11]([OH:13])=[O:12])[CH2:7][CH2:8][S:9][CH3:10].[Cl-].[Al+3].[Cl-].[Cl-].[Br:22]Br>C(O)(=O)C>[NH2:1][C:2]1[CH:17]=[CH:16][C:15]([Br:22])=[CH:14][C:3]=1[CH2:4][NH:5][C@H:6]([C:11]([OH:13])=[O:12])[CH2:7][CH2:8][S:9][CH3:10]

Participants

5

Reactant 3

HCID 24408Bromine2×HCID 6451240Aluminum(III) ChlorideHCID 13340364N-[(2-Aminophenyl)methyl]-L-methionine

Product 1

HCID 13340370HCID 13340370, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

2.54 gm (0.01 mol) of N-(2-amino-benzyl)-methionine and 100 gm of aluminum chloride were dissolved in 50 cc of anhydrous acetic acid while gently heating. Then, the mixture was brought to room temperature and, while stirring, 0.52 cc (0.01 mol) of bromine diluted in 20 cc of acetic acid was added slowly. A light-colored precipitate was formed. After the addition of bromine was finished, the precipitate was centrifuged off, washed with ample acetic acid and then with anhydrous ether, and dried in a dryer. Then, the product was dissolved in 40 cc of water, and the pH of the solution was adjusted to 6 by addition of dilute ammonia while cooling it on an ice water bath. The mixture was allowed to stand for 24 hours, whereupon the new precipitate was centrifuged off, washed with water and dried in drying chamber. (Solvent of the crystallizate: alcohol at 50° C.). The melting point of the product was 207° C., and the yield was 45% of theory.

Workup

  1. temperaturewhile gently heating
  2. customwas brought to room temperature
  3. additionwas added slowly
  4. customA light-colored precipitate was formed
  5. washwashed with ample acetic acid
  6. dry with materialwith anhydrous ether, and dried in a dryer
  7. dissolutionThen, the product was dissolved in 40 cc of water
  8. additionthe pH of the solution was adjusted to 6 by addition of dilute ammonia
  9. temperaturewhile cooling it on an ice water bath
  10. washwashed with water
  11. customdried
  12. customin drying chamber
  13. customat 50° C.
  14. customwas 207° C.

Sources & evidence

ORD record
ord-9258067c1cdb4ef1a29429ae6fb9ac5f
Source dataset
uspto-grants-1980_01
Patent number
US04185114

Reaction notes

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