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

HRID 232364
Notes
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Reaction equation

HRID 232364 reaction equation
Cl.[NH2:2][CH2:3][C@H:4]1[O:8][C@@H:7]([N:9]2[CH:16]=[C:15]([CH2:17][CH2:18][Cl:19])[C:13](=[O:14])[NH:12][C:10]2=[O:11])[CH2:6][C@@H:5]1[OH:20].C1C=CC=CC=1.[Cl:27][C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([Cl:34])[C:29]=1[CH2:35][C:36](Cl)=[O:37].C(Cl)(=O)C(Cl)=O>O.[OH-].[Na+].CO.C(O)C>[Cl:19][CH2:18][CH2:17][C:15]1[C:13](=[O:14])[NH:12][C:10](=[O:11])[N:9]([CH:16]=1)[C@@H:7]1[O:8][C@H:4]([CH2:3][NH:2][C:36](=[O:37])[CH2:35][C:29]2[C:28]([Cl:27])=[CH:33][CH:32]=[CH:31][C:30]=2[Cl:34])[C@@H:5]([OH:20])[CH2:6]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 241BenzeneHCID 65578Oxalyl chlorideHCID 27581482-(2,6-Dichlorophenyl)acetyl chlorideHCID 679265535'-Amino-5-(2-chloroethyl)-2',5'-dideoxyuridine hydrochloride

Product 1

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

Reagents, catalysts & solvents 4

HCID 702EthanolSolvent
HCID 887MethanolSolvent
HCID 962WaterSolvent2×
HCID 14798Sodium HydroxideSolvent

Procedure

0.32 g of 5'-amino-5-(2-chloroethyl)-2',5'-dideoxyuridine 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-77e7c4a566c04162909405c77b957cfa
Source dataset
uspto-grants-1989_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04851519

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes