Nitrogen mustard hydrochloride → HCID 20344006, compound

HRID 2049687Notes

Reaction equation

HRID 2049687 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 one 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 successively washed with one 25 ml portion of a saturated sodium chloride solution and dried, providing 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 one 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 successively washed with one 25 ml portion of a saturated sodium chloride solution
  9. customdried

Sources & evidence

ORD record
ord-4058cdeebc1b4e558cc55ae99a197e23
Source dataset
uspto-grants-1980_04
Patent number
US04198420

Reaction notes

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