Water → HCID 2954358, compound

HRID 2393234Notes

Reaction equation

HRID 2393234 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]=[C:11]=[O:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl.[NH2:14][C:15]1[CH:16]=[C:17]([C:25]([O:27][CH3:28])=[O:26])[CH:18]=[C:19]([CH:24]=1)[C:20]([O:22][CH3:23])=[O:21].O>C(Cl)Cl.C(OCC)(=O)C>[CH3:28][O:27][C:25]([C:17]1[CH:16]=[C:15]([NH:14][C:11]([NH:10][C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=2)=[O:12])[CH:24]=[C:19]([C:20]([O:22][CH3:23])=[O:21])[CH:18]=1)=[O:26]

Participants

6

Reactant 3

HCID 962WaterHCID 66012Benzene, 1-isocyanato-4-nitro-HCID 18974694HCID 18974694, compound

Product 1

HCID 2954358HCID 2954358, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-nitrophenylisocyanate (2.17 g, 12.83 mmol) in anhydrous DCM (15 ml) was added dropwise to a stirred suspension of dimethyl 5-aminoisophthalate (7.23) (2.71 g, 12.83 mmol) in DCM (35 ml). The reaction mixture was stirred for 1 h under an inert atmosphere after which it was diluted with ethyl acetate (100 ml) to dissolve a yellow precipitate which had formed during the reaction. This gave a yellow solution which formed a white precipitate on addition of water (30 ml). The precipitate was collected by filtration, repeatedly washed with water, and dried under reduced pressure. This gave a white solid which was recrystallised from acetone/petrol 40-60 to give the title compound 7.67 as a white powder (2.53 g, 53%). M.p. 193°-195° C.; m/z (+EI) 748 (5%, 2M+H+), 374 (100%, M+H+), 373 (32%, M), 342 (35%, M+H+-OMe); δH (250 MHz, d6 -DMSO) 3.85 (s, 6H, 2×OCH3), 7.70 (2H, d, J 7.5 Hz, 2×Ar--H), 8.10 (1H, s, Ar--H), 8.25 (2H, d, J 7.5 Hz, 2×Ar--H) 8.40 (2H, s, Ar--H), 9.50 (1H, s, NH), 9.55 (1H, s, NH); δC (62.5 MHz, CD3OD) 52.96. 118.28, 123.40, 123.65, 131.13, 140.65, 141.73, 146.43, 152.41, 165.74; RF 0.19 [DCM/methanol (95:5)].

Workup

  1. dissolutionto dissolve a yellow precipitate which
  2. customhad formed during the reaction
  3. customThis gave a yellow solution which
  4. customformed a white precipitate
  5. filtrationThe precipitate was collected by filtration
  6. washrepeatedly washed with water
  7. customdried under reduced pressure
  8. customThis gave a white solid which
  9. customwas recrystallised from acetone/petrol 40-60

Sources & evidence

ORD record
ord-9ecdae81bbbe4c3a92d2bb9f37f1beb8
Source dataset
uspto-grants-1998_09
Patent number
US05807688

Reaction notes

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