N,O-Dimethylhydroxylamine → HCID 13371782, compound

HRID 745887Notes

Reaction equation

HRID 745887 reaction equation
[CH3:1][C:2]1[CH:14]=[C:13]([CH3:15])[N:5]2[S:6](=[O:12])(=[O:11])[NH:7][C:8](=[O:10])[N:9]=[C:4]2[N:3]=1.[CH3:16][O:17][NH:18][CH3:19]>C(Cl)Cl>[CH3:16][O:17][N:18]([S:6]([NH:7][C:8]([NH:9][C:4]1[N:3]=[C:2]([CH3:1])[CH:14]=[C:13]([CH3:15])[N:5]=1)=[O:10])(=[O:12])=[O:11])[CH3:19]

Participants

4

Reactant 2

HCID 14232N,O-DimethylhydroxylamineHCID 133717746,8-Dimethyl-1H-1lambda~6~-pyrimido[1,2-b][1,2,4,6]thiatriazine-1,1,3(2H)-trione

Product 1

HCID 13371782HCID 13371782, compoundYield 67.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

5.7 g (0.025 mol) of 2,3-dihydro-6,8-dimethyl-3-oxopyrimidino-[1,2-b][1,2,4,6]-thiatriazine 1,1-dioxide (cf. Example 1) are suspended in 100 ml of methylene dichloride, and 3.05 g (0.05 mol) of O,N-dimethylhydroxylamine--dissolved in 50 ml of methylene dichloride--are added at -40° C. in the course of one hour. The mixture is stirred for a further 18 hours at room temperature and evaporated to dryness, and the residue is taken up in water and acidified to pH 4--5 with 0.5 N HCl. After extraction with methylene dichloride, the mixture is worked up as under Example 17. 4.9 g (67.8% of theory) of 1-[(N-methoxy-N-methylamino)-sulfonyl]-3-(4,6-dimethyl-2-pyrimidinyl)-urea of melting point 152° C. are obtained.

Workup

  1. additionare added at -40° C. in the course of one hour
  2. customevaporated to dryness
  3. extractionAfter extraction with methylene dichloride

Sources & evidence

ORD record
ord-dcd47163bf4449559e8b6806395e4f7f
Source dataset
uspto-grants-1986_07
Patent number
US04601747

Reaction notes

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