Reaction equation
IC1C=C(I)C=C(I)C=1C1C=CC(C)=CC=1.[I:17][C:18]1[C:23]([CH2:24][CH3:25])=[C:22]([I:26])[C:21]([CH2:27][CH3:28])=[C:20]([I:29])[C:19]=1[C:30]1[CH:35]=[CH:34][C:33]([C:36](O)=[O:37])=[C:32]([N+:39]([O-:41])=[O:40])[CH:31]=1.S(Cl)([Cl:44])=O>[Zn]>[I:17][C:18]1[C:23]([CH2:24][CH3:25])=[C:22]([I:26])[C:21]([CH2:27][CH3:28])=[C:20]([I:29])[C:19]=1[C:30]1[CH:35]=[CH:34][C:33]([C:36]([Cl:44])=[O:37])=[C:32]([N+:39]([O-:41])=[O:40])[CH:31]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Freidel-Crafts acylation is performed on 2′,4′,6′-triiodo-3′-ethyl-3-nitrobiphenyl-4-carboxylic acid (13) in the presence of AlCl3 and CH3COCl to yield 2′,4′,6′-triiodo-3′-ethyl-5′-acetyl-3-nitrobiphenyl-4-carboxylic acid (17). 2′,4′,6′-triiodo-3′-ethyl-5′-acetyl-3-nitrobiphenyl-4-carboxylic acid (17) is then reacted with a zinc mercury amalgam and hydrochloric add and heated to yield 2′,4′,6′-triiodo-3′,5′-bis(ethyl)-3-nitrobiphenyl-4-carboxylic acid (18). C 15 H 10 I 3 N O 4 → C H 3 C O Cl Al Cl 3 → Δ Zn ( Hg ) , H Cl C 17 H 14 I 3 N O 4 2′,4′,6′-triiodo-3′,5′-bis(ethyl)-3-nitrobiphenyl-4-carboxylic acid (18) is reacted with thionyl chloride to yield 2′,4′,6′-triiodo-3′,5′-bis(ethyl)-3-nitrobiphenyl-4-carbonyl chloride (19). C 17 H 14 I 3 N O 4 → S O Cl 2 C 17 H 13 Cl I 3 N O 3 1,3,4,6-tetra-O-acetyl-D-glucosamine (9) is reacted with 2′,4′,6′-triiodo-3′5′-bis(ethyl)-3-nitrobiphenyl-4-carbonyl chloride (19) to yield 2-nitro-4-[3′,5′-bis(ethyl)-2′,4′,6′-triiodophenyl]-benzoyl-1,3,4,6-tetra-O-acetyl-D-glucosamine (20). C14H21NO9+C17H13ClI3NO3→C31H33I3N2O12 2-nitro-4-[3′,5′-bis(ethyl)-2′,4′,6′-triiodophenyl]-benzoyl-1,3,4,6-tetra-O-acetyl-D-glucosamine (20) is oxidized with potassium permanganate to yield 2-nitro-4-[3′,5′-bis(carboxylic acid)-2′,4′,6′-triiodophenyl]-benzoyl-1,3,4,6-tetra-O-acetyl-D-glucosamine (21). C 31 H 33 I 3 N 2 O 12 → K Mn O 4 C 29 H 25 I 3 N 2 O 16 2-nitro-4-[3′,5′-bis(carboxylic acid)-2′,4′,6′-triiodophenyl]-benzoyl-1,3,4,6-tetra-O-acetyl-D-glucosamine (21) is reacted with ethanol and weak hydrochloric acid and heated to yield 2-nitro-4-[3′,5′-bis(ethoxycarbonyl)-2′,4′,6′-triiodophenyl]-benzoyl-1,3,4,6-tetra-O-acetyl-D-glucosamine (22). C 29 H 25 I 3 N 2 O 16 → Δ Et O H , H Cl C 33 H 33 I 3 N 2 O 16 2-nitro-4-[3′,5′-bis(ethoxycarbonyl)-2′,4′,6′-triiodophenyl]-benzoyl-1,3,4,6-tetra-O-acetyl-D-glucosamine (22) is reacted with methylamine to yield 2-nitro-4-[3′,5′-bis(N-methylcarboxamide)-2′,4′,6′-triiodophenyl]-benzoyl-1,3,4,6-tetra-O-acetyl-D-glucosamine (23). C 33 H 33 I 3 N 2 O 16 → C H 3 N H 2 C 31 H 31 I 3 N 4 O 14 2-nitro-4-[3′,5′-bis(N-methylcarboxamide)-2′,4′,6′-triiodophenyl]-benzoyl-1,3,4,6-tetra-O-acetyl-D-glucosamine (23) is treated with stannous chloride and hydrochloric acid to yield 2-amino-4-[3′,5′-bis(N-methylcarboxamide)-2′,4′,6′-triiodophenyl]-benzoyl-D-glucosamine (24). C 31 H 31 I 3 N 4 O 14 → Sn Cl 2 , H Cl C 23 H 25 I 3 N 4 O 8
Sources & evidence
- ORD record
- ord-3f75c2c0e3dc4edca68f28f2e1095f9f
- Source dataset
- uspto-grants-2005_08
- Patent number
- US06923950B2
Linked notes
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