Nitrogen mustard hydrochloride → HCID 20344006, compound

HRID 2049869Notes

Reaction equation

HRID 2049869 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([S:10][C:11]2[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=2[CH2:13][C:14]#[N:15])=[CH:6][CH:5]=1.[CH3:20][N:21]([CH2:25][CH2:26]Cl)[CH2:22][CH2:23]Cl.Cl>CS(C)=O>[C:14]([C:13]1([C:12]2[CH:16]=[CH:17][CH:18]=[CH:19][C:11]=2[S:10][C:7]2[CH:8]=[CH:9][C:4]([F:3])=[CH:5][CH:6]=2)[CH2:26][CH2:25][N:21]([CH3:20])[CH2:22][CH2:23]1)#[N:15]

Participants

5

Reactant 3

HCID 5935Nitrogen mustard hydrochlorideHCID 24758Sodium hydrideHCID 20343961HCID 20343961, compound

Product 1

HCID 20344006HCID 20344006, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

2.3 g of 99% sodium hydride are slowly added to a mixture, under nitrogen, of 4.3 g of 2-(4-fluorophenylthio)-benzyl cyanide in 30 mls of dimethylsulfoxide. After total addition, the mixture is stirred for an additional five minutes and then a mixture of 3.9 g of 95% mechlorethamine hydrochloride in 20 ml of dimethylsulfoxide is added portionwise over a 40 minute span. After this addition, the reaction is stirred for 1 hour in a hot water bath at 70° C. and then permitted to stand at ambient temperature for 16 hours. The cooled reaction mixture is poured onto 150 ml of crushed ice and the diluted mixture is extracted thrice with 60 ml portions of ether. The combined ether extracts are washed with 25 ml of saturated sodium chloride solution and dried, leaving a solid. The solid is recrystallized from cyclohexane, leaving the pure product, 4-cyano-4-[2-(4-fluorophenylthio)phenyl]-1-methylpiperidine.

Workup

  1. additionAfter total addition
  2. additionis added portionwise over a 40 minute span
  3. additionAfter this addition
  4. stirringthe reaction is stirred for 1 hour in a hot water bath at 70° C.
  5. waitto stand at ambient temperature for 16 hours
  6. customThe cooled reaction mixture
  7. extractionthe diluted mixture is extracted thrice with 60 ml portions of ether
  8. washThe combined ether extracts are washed with 25 ml of saturated sodium chloride solution
  9. customdried
  10. customleaving a solid
  11. customThe solid is recrystallized from cyclohexane

Sources & evidence

ORD record
ord-efa73cfa827d4736811e5f768b4bc16d
Source dataset
uspto-grants-1980_04
Patent number
US04198419

Reaction notes

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