Benzoic acid, 2-(isocyanatosulfonyl)-, methyl ester → HCID 19871557, compound

HRID 329759Notes

Reaction equation

HRID 329759 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[N:9]=[C:8]([S:10][CH3:11])[N:7]=[C:6]([NH2:12])[N:5]=1.[CH3:13][O:14][C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[S:23]([N:26]=[C:27]=[O:28])(=[O:25])=[O:24])=[O:16]>C(Cl)Cl>[CH3:1][O:2][CH2:3][C:4]1[N:9]=[C:8]([S:10][CH3:11])[N:7]=[C:6]([NH:12][C:27]([NH:26][S:23]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[C:15]([O:14][CH3:13])=[O:16])(=[O:25])=[O:24])=[O:28])[N:5]=1

Participants

4

Reactant 2

HCID 156281Benzoic acid, 2-(isocyanatosulfonyl)-, methyl esterHCID 22349738HCID 22349738, compound

Product 1

HCID 19871557HCID 19871557, compoundYield 92.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.8 g of 4-methoxymethyl-6-methylthio-2-amino-1,3,5-triazine in 15 ml of anhydrous methylene chloride was added 1.5 g of 2-methoxycarbonylbenzenesulfonylisocyanate. The mixture was heated for one hour and then stirred at ambient temperature for 18 hours. Solvent was removed in vacuo and the residue was triturated with 1-chlorobutane (50 ml) and filtered to give 1.7 g of the desired product, m.p. 147°-149° C. mmr: 2.6 ppm δ, 3H; 3.4 ppm δ, 3H; 3.85 ppm δ, 3H; 4.45 δ, 2H; 7.65-8.5 broad, 4H.

Workup

  1. temperatureThe mixture was heated for one hour
  2. customSolvent was removed in vacuo
  3. customthe residue was triturated with 1-chlorobutane (50 ml)
  4. filtrationfiltered

Sources & evidence

ORD record
ord-6df5f708cb644fbca934ecd4b3e3e1a7
Source dataset
uspto-grants-1990_01
Patent number
US04892946

Reaction notes

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