Dichloromethane → HCID 14653253, compound

HRID 893307Notes

Reaction equation

HRID 893307 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:13](=[O:14])[C:12]2[CH:15]=[C:16]([S:18](Cl)(=[O:20])=[O:19])[S:17][C:11]=2[N:10]=[C:9]1[CH3:22].ClCCl.[C:26]([NH:29][CH2:30][CH2:31][CH2:32][CH2:33][NH2:34])(=[O:28])[CH3:27]>C(N(CC)CC)C>[C:26]([NH:29][CH2:30][CH2:31][CH2:32][CH2:33][NH:34][S:18]([C:16]1[S:17][C:11]2[N:10]=[C:9]([CH3:22])[N:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])[C:13](=[O:14])[C:12]=2[CH:15]=1)(=[O:20])=[O:19])(=[O:28])[CH3:27]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 122356N-AcetylputrescineHCID 14653249HCID 14653249, compound

Product 1

HCID 14653253HCID 14653253, compoundYield 44.4%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To 8.0 g of 3,4-dihydro-3-(2-chlorophenyl)-6-chlorosulfonyl-2-methyl-4-oxothieno[2,3-d]pyrimidine were added 150 ml of dichloromethane, 3.3 g of 4-acetylaminobutylamine and 5.9 ml of triethylamine, and the mixture was stirred at room temperature for 3 hours. After the reaction mixture was washed with water, the concentrated residue was purified by means of silica gel chromatography to obtain 5.71 g of oily substance, which was crystallized from ethyl acetate-hexane to afford 4.44 g of the title compound, m.p. 203°-206° C. (decomposition).

Workup

  1. washAfter the reaction mixture was washed with water
  2. customthe concentrated residue was purified by means of silica gel chromatography
  3. customto obtain 5.71 g of oily substance, which
  4. customwas crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-81970c0306e64cffb22348a16924ca0e
Source dataset
uspto-grants-1992_06
Patent number
US05124331

Reaction notes

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