Hydrochloric Acid → HCID 20343959, 화합물

HRID 2049864노트

반응식

HRID 2049864 반응식
[H-].[Na+].[C:3]1([S:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH2:16][C:17]#[N:18])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:19][N:20]([CH2:24][CH2:25]Cl)[CH2:21][CH2:22][Cl:23].Cl.Cl>CN(C)C=O.CCOCC>[ClH:23].[C:17]([C:16]1([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[S:9][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:25][CH2:24][N:20]([CH3:19])[CH2:21][CH2:22]1)#[N:18]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 5935Nitrogen mustard hydrochlorideHCID 24758Sodium hydrideHCID 123285452-(Phenylthio)benzeneacetonitrile

생성물 1

HCID 20343959HCID 20343959, 화합물

시약·촉매·용매 2

HCID 3283Diethyl Ether용매3회HCID 6228Dimethylformamide용매2회

실험 절차

2.6 g of 99% sodium hydride are added portionwise to a solution of 4.4 g of 2-(phenylthio)phenylacetonitrile in 50 ml of dimethylformamide. The resulting reddish brown mixture is stirred for 30 minutes before adding dropwise a solution of 4.0 g of mechlorethamine hydrochloride in 50 ml of dimethylformamide, maintaining gas evolution at a slow rate. After total addition, the mixture is stirred at 80°-85° C. for 15 hours. Thereafter, 100 g of ice are added before the mixture is extracted thrice with ether. The combined ether extracts are dried over potassium carbonate and then the solvent is removed under vacuum leaving a brownish oil. The oil is dissolved in a small amount of ether and passed through, with additional ether, an alumina column which is packed in ether. The effluent is concentrated leaving an oil which is converted to its hydrochloride which is recrystallized from an acetone-ether mixture, leaving 4-cyano-1-methyl-4-(2-phenylthiophenyl)piperidine hydrochloride.

후처리

  1. temperaturemaintaining gas evolution at a slow rate
  2. additionAfter total addition
  3. stirringthe mixture is stirred at 80°-85° C. for 15 hours
  4. extractionis extracted thrice with ether
  5. dry with materialThe combined ether extracts are dried over potassium carbonate
  6. customthe solvent is removed under vacuum
  7. customleaving a brownish oil
  8. concentrationThe effluent is concentrated
  9. customleaving an oil which
  10. customis recrystallized from an acetone-ether mixture

출처 및 근거

ORD 기록
ord-d9faa95ae7334c51a3448028224a7fcf
출처 데이터셋
uspto-grants-1980_04
특허 번호
US04198419

반응 노트

불러오는 중…