Sodium hydride → HCID 15279948, compound

HRID 1939611Notes

Reaction equation

HRID 1939611 reaction equation
[H-].[Na+].[O:3]1[CH2:8][CH2:7][O:6][C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[S:15]([NH2:18])(=[O:17])=[O:16])=[N:4]1.[O:19]([C:26]([NH:28][C:29]1[N:34]=[C:33]([O:35][CH3:36])[CH:32]=[C:31]([O:37][CH3:38])[N:30]=1)=O)C1C=CC=CC=1>C(#N)C>[CH3:36][O:35][C:33]1[CH:32]=[C:31]([O:37][CH3:38])[N:30]=[C:29]([NH:28][C:26]([NH:18][S:15]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[C:5]2[O:6][CH2:7][CH2:8][O:3][N:4]=2)(=[O:16])=[O:17])=[O:19])[N:34]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 10922715HCID 10922715, compoundHCID 10945667Carbamic acid, N-(4,6-dimethoxy-2-pyrimidinyl)-, phenyl ester

Product 1

HCID 15279948HCID 15279948, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

0.79 g (0.033 mol) of sodium hydride are added under argon to a mixture of 4.0 g (0.017 mol) of 2-(5,6-dihydro-[1,4,2]-dioxazin-3-yl)benzenesulphonamide and 4.6 g (0.017 mol) of 2-phenoxycarbonylamino-4,6-dimethoxypyrimidine in 20 ml of absolute acetonitrile, and the mixture is stirred at room temperature for 18 hours. The precipitate is filtered off with suction and stirred up with a 20% solution of sodium dihydrogen phosphate. The precipitate is filtered off with suction and dried under high vacuum. 3.9 g (56% of theory) of N-(4,6-dimethoxypyrimidin-2-yl)-N'-(2-(5,6-dihydro-[1,4,2]-dioxazin-3-yl)benzenesulphonyl)-urea are obtained with a melting point of 189° C.

Workup

  1. filtrationThe precipitate is filtered off with suction
  2. stirringstirred up with a 20% solution of sodium dihydrogen phosphate
  3. filtrationThe precipitate is filtered off with suction
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-9906055f2fa9465cb45906dcb5afcff6
Source dataset
uspto-grants-1997_12
Patent number
US05696257

Reaction notes

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