Dichloromethane → Methyl 2-{[(4,5,6-trimethylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl}benzoate

HRID 66444

Reaktionsgleichung

Reaktionsgleichung von HRID 66444
[NH2:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([CH3:9])=[C:4]([CH3:10])[N:3]=1.C(Cl)Cl.[N:14]([S:17]([C:20]1[CH:29]=[CH:28][CH:27]=[CH:26][C:21]=1[C:22]([O:24][CH3:25])=[O:23])(=[O:19])=[O:18])=[C:15]=[O:16]>C(Cl)CCC>[CH3:10][C:4]1[C:5]([CH3:9])=[C:6]([CH3:8])[N:7]=[C:2]([NH:1][C:15]([NH:14][S:17]([C:20]2[CH:29]=[CH:28][CH:27]=[CH:26][C:21]=2[C:22]([O:24][CH3:25])=[O:23])(=[O:19])=[O:18])=[O:16])[N:3]=1

Komponenten

5

Edukt 3

HCID 6344DichloromethaneHCID 156281Benzoic acid, 2-(isocyanatosulfonyl)-, methyl esterHCID 122508624,5,6-Trimethylpyrimidin-2-amine

Produkt 1

HCID 13038388Methyl 2-{[(4,5,6-trimethylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl}benzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8005Butyl ChlorideLösungsmittel

Versuchsvorschrift

To a mixture of 1.0 gram (0.0073 mole) of 2-amino-4,5,6-trimethylpyrimidine and 5.0 ml of dried methylene chloride stirring magnetically in a 50 ml RB single neck flask, 2.1 grams of methyl 2-(isocyanatosulfonyl)benzoate was added at room temperature and the mixture stirred at room temperature for 24 hours. Butyl chloride (4 ml) was added with constant stirring and the insoluble product filtered, washed immediately with butyl chloride and dried. (Yield 1.3 grams, m.p. 152°-161°). IR (Nujol): 5.60, 5.75 (C=O), 11.25 11.90 microns; NMR (TFA-d): δ2.30 (s,3H,CH3), 2.65 (s, 6H, 2CH3), 4.00 (s, 3H, CO2CH3), 7.60-8.60 (m, ArH).

Aufarbeitung

  1. stirringwith constant stirring
  2. filtrationthe insoluble product filtered
  3. washwashed immediately with butyl chloride
  4. customdried

Quellen und Nachweise

ORD-Eintrag
ord-d5dab4561c9d452a95c1e193556c737d
Quelldatensatz
uspto-grants-1982_08
Patentnummer
US04342587

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