Benzoic acid, 2-(isocyanatosulfonyl)-, methyl ester → Methyl 2-[[(4-methylquinazolin-2-yl)aminocarbonyl]aminosulfonyl]benzoate

HRID 1155939Notes

Reaction equation

HRID 1155939 reaction equation
[NH2:1][C:2]1[N:11]=[C:10]([CH3:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[C:13]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[S:23]([N:26]=[C:27]=[O:28])(=[O:25])=[O:24])([O:15][CH3:16])=[O:14]>C(#N)C>[CH3:12][C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=[C:2]([NH:1][C:27]([NH:26][S:23]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[C:13]([O:15][CH3:16])=[O:14])(=[O:25])=[O:24])=[O:28])[N:11]=1

Participants

4

Reactant 2

HCID 156281Benzoic acid, 2-(isocyanatosulfonyl)-, methyl esterHCID 2693254-methylquinazolin-2-amine

Product 1

HCID 14774717Methyl 2-[[(4-methylquinazolin-2-yl)aminocarbonyl]aminosulfonyl]benzoateYield 41.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 20 ml dry acetonitrile was added 1.0 g of 2-amino-4-methylquinazoline followed by 3.1 g of 2-carbomethoxybenzenesulfonyl isocyanate. The slurry was refluxed for 2 hours and allowed to stand at ambient temperature for 16 hours. The light yellow solid was filtered, washed with acetonitrile and dried to yield 1.04 g of methyl 2-[[(4-methylquinazolin-2-yl)aminocarbonyl]aminosulfonyl]benzoate, m.p. 182°-183°. The product showed characteristic absorption bands in the infrared spectrum at 1730 and 1700 cm-1 and at 2.9, 3.9 and 7.5-8.4 ppms in the nuclear magnetic resonance spectrum (60 MHz), indicating the title compound.

Workup

  1. temperatureThe slurry was refluxed for 2 hours
  2. filtrationThe light yellow solid was filtered
  3. washwashed with acetonitrile
  4. customdried

Sources & evidence

ORD record
ord-55a4651a7b334efa8a1bbc9f680f2543
Source dataset
uspto-grants-1982_06
Patent number
US04333760

Reaction notes

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