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

HRID 66444

Reaction equation

HRID 66444 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8005Butyl ChlorideSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-d5dab4561c9d452a95c1e193556c737d
Source dataset
uspto-grants-1982_08
Patent number
US04342587

Linked notes

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