2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 135500131, compound

HRID 1684109Notes

Reaction equation

HRID 1684109 reaction equation
[Br:1][CH2:2][C:3]1[NH:4][C:5](=[O:22])[C:6]2[C:7]([N:21]=1)=[C:8]([OH:20])[C:9]1[C:10](=[O:19])[NH:11][C:12]([CH2:17][Br:18])=[N:13][C:14]=1[C:15]=2[OH:16].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.C(O)CCC.C(O)(=O)C.O.[K+].[Br-]>CO>[Br:18][CH2:17][C:12]1[NH:11][C:10](=[O:19])[C:9]2[C:8](=[O:20])[C:7]3[N:21]=[C:3]([CH2:2][Br:1])[NH:4][C:5](=[O:22])[C:6]=3[C:15](=[O:16])[C:14]=2[N:13]=1

Participants

6

Reactant 4

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 253877Potassium BromideHCID 22056973Butanol acetic acid waterHCID 135404972HCID 135404972, compound

Product 1

HCID 135500131HCID 135500131, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 105 mg (0.244 mmol) of 18 suspended in 15 mL of dry methanol, was added 61 mg (0.268 mmol) of dichlorodicyanobenzoquinone (DDQ) and the reaction left to stir at room temperature for 1 hour. The solids were filtered off, washed with methanol, and dried to afford pure 19: 95 mg (91%) yield; dec pt 274°-275° C.; TLC (n-butanol/acetic acid/water [5:2:3]), Rf =0.46; IR (KBr pellet) 3062, 3040, 2990, 2933, 1713, 1645, 1576, 1547, 1480, 1142 cm-1 ; 1H NMR (dimethyl-d6 sulfoxide) δ4.45 (4H, s, methylenes); mass spectrum (EI, solids probe), m/z 428, 430, and 432 (P+ for the 79Br, 79Br; 79Br, 81Br, 81Br, 81Br combinations, respectively, in an intensity ratio of 1:2:1). Anal. Calcd for C12H6Br2N4O4 ; C, 33.52; H, 1.41; N, 13.03. Found: C, 33.89; H, 1.31; N, 12.50.

Workup

  1. waitthe reaction left
  2. filtrationThe solids were filtered off
  3. washwashed with methanol
  4. customdried
  5. customto afford pure 19
  6. custom95 mg (91%) yield

Sources & evidence

ORD record
ord-e782cd09779a465a8bb0a9a91a053d03
Source dataset
uspto-grants-1997_06
Patent number
US05639881

Reaction notes

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