Cystamine Dihydrochloride → Bis-DNP-cystamine

HRID 704545

反応式

HRID 704545 の反応式
Cl.Cl.[NH2:3][CH2:4][CH2:5][S:6][S:7][CH2:8][CH2:9][NH2:10].[N+:11]([C:14]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:16][C:15]=1F)([O-:13])=[O:12].C([O-])([O-])=O.[K+].[K+]>O>[N+:11]([C:14]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:16][C:15]=1[NH:3][CH2:4][CH2:5][S:6][S:7][CH2:8][CH2:9][NH:10][C:15]1[CH:16]=[CH:17][C:18]([N+:20]([O-:22])=[O:21])=[CH:19][C:14]=1[N+:11]([O-:13])=[O:12])([O-:13])=[O:12]

参加物

5

反応物 3

HCID 5941Cystamine DihydrochlorideHCID 6264DinitrofluorobenzeneHCID 11430Potassium Carbonate

生成物 1

HCID 368190Bis-DNP-cystamine

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
75 °C

実験手順

A 25 mL round-bottom flask fitted with a magnetic stirrer was charged with 225 mg (1.0 mmol) of cystamine dihydrochloride, 409 mg (2.2 mmol) 2,4-dinitrofluorobenzene, 25 mg of K2CO3, and 10 mL of H2O. The mixture then stirred in a 75° C. oil bath for 18 h. After cooling, the solvent was decanted from a yellow insoluble sludge. The sludge crystallized on trituration with 10 mL of CH2Cl2. The yellow crystals were washed with additional CH2Cl2 and recrystallized from 0.5 mL of 15:85 H2O/DMF. The isolated product was washed with 1:1 H2O/DMF affording 77 mg of N,N'-bis-(2,4-dinitrophenyl) cystamine, mp 175°-176° C. Calcd for C16H16N6O8S2:C, 39.67; H, 3.31; N, 17.36; S, 13.22. Found: C, 39.74; H, 3.38; N, 17.26; S, 13.48. 200 MHz NMR (DMSO-d6): 3.08 (t, J =6.6, 4H), 3.80 (4 lines, 4H), 7.27 (d, J =9.6, 2H), 8.25 (dd, J =2.8, 9.6, 2H), 8.84 (dd, J =2.8, 0.8, 2H), 8.93 (t, J=5.6, 2H).

後処理

  1. customA 25 mL round-bottom flask fitted with a magnetic stirrer
  2. temperatureAfter cooling
  3. customthe solvent was decanted from a yellow insoluble sludge
  4. customThe sludge crystallized on trituration with 10 mL of CH2Cl2
  5. washThe yellow crystals were washed with additional CH2Cl2
  6. customrecrystallized from 0.5 mL of 15:85 H2O/DMF
  7. washThe isolated product was washed with 1:1 H2O/DMF affording 77 mg of N,N'-bis-(2,4-dinitrophenyl) cystamine, mp 175°-176° C

出典と根拠

ORDレコード
ord-b00a07bddc02439f84c721a9ade65321
出典データセット
uspto-grants-1991_01
特許番号
US04988625

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