Iodine → HCID 14839507, compound

HRID 2107556Notes

Reaction equation

HRID 2107556 reaction equation
II.[N:3]1[CH:8]=[CH:7][CH:6]=[N:5][C:4]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][CH2:18][C:19](=O)[CH3:20])[CH2:11][CH2:10]1.[NH2:22][C:23]([NH2:25])=[S:24]>O>[N:3]1[CH:8]=[CH:7][CH:6]=[N:5][C:4]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][CH2:18][C:19]2[N:22]=[C:23]([NH2:25])[S:24][CH:20]=2)[CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 807IodineHCID 2723790ThioureaHCID 14839498HCID 14839498, compound

Product 1

HCID 14839507HCID 14839507, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

Iodine, 6.34 g, is added in small portions to a mixture of 6 g of 6-[4-(2-pyrimidinyl)-1-piperazinyl]-2-hexanone (Example A) and 3.8 g of thiourea. The resulting paste is heated at 110° C. overnight. The mixture is taken up into boiling water, filtered, and basified with ammonium hydroxide. Dichloromethane is used to extract the products which are purified by silica gel chromatography to afford 2 g of recovered starting ketone, 0.8 g of 4-methyl-5-[3-[4-(2-pyrimidinyl)-1-piperazinyl]propyl]-2-thiazolamine (Example 1); mp 152°-156° C.; and 1.2 g of 4-[4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl]-2-thiazolamine (Example 1a); mp 101°-104° C.

Workup

  1. filtrationfiltered
  2. extractionto extract the products which
  3. customare purified by silica gel chromatography
  4. customto afford 2 g
  5. customof recovered

Sources & evidence

ORD record
ord-cfbea890444642b0a820911574a8cd48
Source dataset
uspto-grants-1990_06
Patent number
US04935424

Reaction notes

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