1-Butanol → HCID 10278583, compound

HRID 860759Notes

Reaction equation

HRID 860759 reaction equation
[Br:1][C:2]1[C:3](Cl)=[N:4][C:5](Cl)=[N:6][CH:7]=1.[S:10]([NH2:20])(=[O:19])([C:12]1[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][CH:13]=1)=[O:11].C([N:24](CC)[CH:25]([CH3:27])[CH3:26])(C)C.C(OCC)C.[CH2:35](O)[CH2:36][CH2:37]C>>[S:10]([C:12]1[CH:13]=[CH:14][C:15]([NH:18][C:5]2[N:4]=[C:3]([NH:24][C:25]3[CH:26]=[CH:37][C:36]([S:10](=[O:19])(=[O:11])[NH2:20])=[CH:35][CH:27]=3)[C:2]([Br:1])=[CH:7][N:6]=2)=[CH:16][CH:17]=1)(=[O:19])(=[O:11])[NH2:20]

Participants

6

Reactant 5

HCID 2631-ButanolHCID 3283Diethyl EtherHCID 5333SulfanilamideHCID 81531DiisopropylethylamineHCID 2899735-Bromo-2,4-dichloropyrimidine

Product 1

HCID 10278583HCID 10278583, compound

Procedure

A solution of 5-bromo-2,4-dichloropyrimidine (228 mg, 1.0 mmol), 4-sulphanilamide (180 mg, 1.05 mmol) and N,N-diisopropylethylamine (174 μl 1.0 mmol) in n-butanol (30 ml) was heated at 100° C. for 16 hours. A gum formed out of solution. Diethyl ether (20 ml) was added, causing the gum to solidify, and further precipitation to occur. The solid was collected by filtration and triturated with hot methanol, giving the title product (55 mg) as a white solid. NMR: (s, 2H), 7.30 (s, 2H), 7.64 (d, 2H), 7.80 (m, 4H), 7.88 (d, 2H), 8.36 (s, 1H), 8.93 (s, 1H), 9.88 (s, 1H).

Workup

  1. customA gum formed out of solution
  2. customfurther precipitation
  3. filtrationThe solid was collected by filtration
  4. customtriturated with hot methanol

Sources & evidence

ORD record
ord-db0b9fd7a96041ff8eca65238ff4a01e
Source dataset
uspto-grants-2006_12
Patent number
US07153964B2

Reaction notes

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