Diethyl Ether → HCID 13559939, compound

HRID 1284410Notes

Reaction equation

HRID 1284410 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:6]=[C:5]([NH2:17])[N:4]=1.[C:18]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[S:28]([N:31]=[C:32]=[O:33])(=[O:30])=[O:29])([O:20][CH3:21])=[O:19].CCOCC>C(#N)C>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][O:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:6]=[C:5]([NH:17][C:32]([NH:31][S:28]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[C:18]([O:20][CH3:21])=[O:19])(=[O:30])=[O:29])=[O:33])[N:4]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 156281Benzoic acid, 2-(isocyanatosulfonyl)-, methyl esterHCID 13559938HCID 13559938, compound

Product 1

HCID 13559939HCID 13559939, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 0.23 g (1.0 mmol) of 4-methoxy-6-(phenoxymethyl)-2-pyrimidinamine in 15 ml dry acetonitrile was added 0.48 g (2.0 mmol) o-carbomethoxybenzenesulfonyl isocyanate and stirred at ambient temperature overnight. Ether was added to the suspension of white solids which were then collected by filtration to afford 0.37 g of the title compound, m.p. 178°-180°. NMR (90 MHz, CDCl3 +DMSO-d6): δ 3.91 (s, 3H); 4.02 (s, 3H); 5.20 (s, 2H); 6.69 (s, 1H); 7.0-7.9 (m, 8H); 8.5 (m, 1H); 9.20 (s, NH); 12.9 (s, NH) ppm; IR (nujol) 1725, 1700 cm-1.

Workup

  1. filtrationwere then collected by filtration

Sources & evidence

ORD record
ord-2bf9519169fd432aa3e9ae9419fa417f
Source dataset
uspto-grants-1986_01
Patent number
US04563211

Reaction notes

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