2,4-Dichloro-6-isocyanato-1,3,5-triazine → 2-(acetoxymethyl)-N-[(4,6-dichloro-1,3,5-triazinyl)aminocarbonyl]benzenesulfonamide

HRID 1155636Notes

Reaction equation

HRID 1155636 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[N:5]=[C:4]([N:9]=[C:10]=[O:11])[N:3]=1.[C:12]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[S:23]([NH2:26])(=[O:25])=[O:24])(=[O:14])[CH3:13]>C(#N)C>[C:12]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[S:23]([NH:26][C:10]([NH:9][C:4]1[N:5]=[C:6]([Cl:8])[N:7]=[C:2]([Cl:1])[N:3]=1)=[O:11])(=[O:24])=[O:25])(=[O:14])[CH3:13]

Participants

4

Reactant 2

HCID 130526242,4-Dichloro-6-isocyanato-1,3,5-triazineHCID 130973012-(Acetoxymethyl)benzenesulfonamide

Product 1

HCID 205372422-(acetoxymethyl)-N-[(4,6-dichloro-1,3,5-triazinyl)aminocarbonyl]benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 4,6-dichloro-1,3,5-triazin-2-yl isocyanate (0.87 g, 4.5 mmol) in acetonitrile (9 ml) was treated with 2-(acetoxymethyl)benzenesulfonamide (1.04 g, 4.5 mmol) and stirred for 16 hours. Volatiles were removed under vacuum to give a residue whose 'H NMR showed δ(CD3)2CO, 8.05-7.80 (m, 1H), 7.65-7.27 (m, 3H), 6.45 (brd s, 1H), 5.50 (s, 2H), 2.10 (s, 3H), consistent with the assigned structure.

Workup

  1. customVolatiles were removed under vacuum
  2. customto give a residue whose 'H NMR

Sources & evidence

ORD record
ord-4325c8c08b354d1c8c3d6bd05c57add0
Source dataset
uspto-grants-1982_06
Patent number
US04332611

Reaction notes

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