Benzene → 5-(2-Chloroethyl)-5'-[2-(2,6-dichlorophenyl)-acetamido]-2',5'-dideoxyuridine

HRID 1085533Notes

Reaction equation

HRID 1085533 reaction equation
Cl.[C@@H]1(N2C=CC(=O)NC2=O)O[C@H](CO)[C@@H](O)[C@H]1O.[NH2:19][CH2:20][C@H:21]1[O:25][C@@H:24]([N:26]2[CH:33]=[C:32]([CH2:34][CH2:35][Cl:36])[C:30](=[O:31])[NH:29][C:27]2=[O:28])[CH2:23][C@@H:22]1[OH:37].C1C=CC=CC=1.[Cl:44][C:45]1[CH:50]=[CH:49][CH:48]=[C:47]([Cl:51])[C:46]=1[CH2:52][C:53](Cl)=[O:54].C(Cl)(=O)C(Cl)=O>O.[OH-].[Na+].CO.C(O)C>[Cl:36][CH2:35][CH2:34][C:32]1[C:30](=[O:31])[NH:29][C:27](=[O:28])[N:26]([CH:33]=1)[C@@H:24]1[O:25][C@H:21]([CH2:20][NH:19][C:53](=[O:54])[CH2:52][C:46]2[C:45]([Cl:44])=[CH:50][CH:49]=[CH:48][C:47]=2[Cl:51])[C@@H:22]([OH:37])[CH2:23]1

Participants

9

Reactant 4

HCID 241BenzeneHCID 65578Oxalyl chlorideHCID 27581482-(2,6-Dichlorophenyl)acetyl chlorideHCID 679266165'-Amino-5-(2-chloroethyl)-2',5'-dideoxyuridine uridine hydrochloride

Product 1

HCID 538312205-(2-Chloroethyl)-5'-[2-(2,6-dichlorophenyl)-acetamido]-2',5'-dideoxyuridine

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 887MethanolSolventHCID 962WaterSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

0.32 g of 5'-amino-5-(2-chloroethyl)-2',5'-dideoxyuridine uridine hydrochloride were dissolved in a mixture of 5 ml of water and 2.5 ml of 1M sodium hydroxide solution. The mixture was shaken vigorously for 25 minutes with a benzene solution of (2,6-dichlorophenyl)acetyl chloride (prepared from 0.22 g of the acid by treatment with oxalyl chloride). The resulting solid was removed by filtration and washed with water and then with diethyl ether to give 0.29 g of crude product of melting point 248°-249° C. (decomposition). 0.1 g of this solid was stirred successively for 1 hour each time with 1 ml of water, 2 ml of ethanol and 2 ml of methanol to give 0.03 g of 5-(2-chloroethyl)-5'-[2-(2,6-dichlorophenyl)-acetamido]-2',5'-dideoxyuridine of melting point 253°-254° C. (decomposition).

Workup

  1. customThe resulting solid was removed by filtration
  2. washwashed with water
  3. customwith diethyl ether to give 0.29 g of crude product of melting point 248°-249° C. (decomposition)

Sources & evidence

ORD record
ord-3cc18515e5e24e8b855a0d125cf7e7a4
Source dataset
uspto-grants-1991_04
Patent number
US05010060

Reaction notes

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