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

HRID 2295245Notes

Reaction equation

HRID 2295245 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): δ 2.30 (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-386588ef84fa434eb4f8ce01f91650b1
Source dataset
uspto-grants-1984_01
Patent number
US04424073

Reaction notes

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