Hydrochloric Acid → HCID 178468779, 화합물

HRID 2253559

반응식

HRID 2253559 반응식
N[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.C(Cl)(Cl)=S.C(OC(C1C=CC([N:28]=[C:29]=[S:30])=CC=1)=O)C.NN.C(OC(C1C=CC([NH:44][NH:45]C(N)=S)=CC=1)=O)C.Cl.[N:50]([O-])=O.[Na+]>C(Cl)(Cl)Cl.O.C(O)C>[CH2:9]([O:8][C:6]([C:5]1[CH:11]=[CH:12][C:2]([C:29]2[SH:30]([NH2:50])[N:45]=[N:44][N:28]=2)=[CH:3][CH:4]=1)=[O:7])[CH3:10]

참가 물질

11

반응물 7

HCID 313Hydrochloric AcidHCID 2337BenzocaineHCID 9321HydrazineHCID 10040ThiophosgeneHCID 71003Ethyl 4-isothiocyanatobenzoateHCID 19745752HCID 19745752, 화합물HCID 23668193Sodium Nitrite

생성물 1

HCID 178468779HCID 178468779, 화합물수율 90%

시약·촉매·용매 3

HCID 702Ethanol용매HCID 962Water용매4회HCID 6212Chloroform용매

반응 조건

온도
5 °C

실험 절차

0.1 Mol of ethyl p-aminobenzoate was mixed with 150 ml of water and stirred for 15 minutes. Thiophosgene (10 g) in 50 ml chloroform was added dropwise. The mixture was stirred for 2 hours at 15° C. The organic solution was washed with HCl 2N, dried and the solvent was removed under vacuum to obtain a yellow-red oil, that was used as crude product. 0.02 mMole of the obtained 4-ethoxycarbonylphenylisothiocyanate and 30 ml ethanol were stirred in a flask and added dropwise with 2 ml 85% hydrazine in 2 ml water. After 15 minutes the crude product separated and was filtered under vacuum. Yield 90%. 0.01 Mole of the obtained 4-ethoxycarbonylphenylthiosemicarbazide was mixed with a solution of 1.5 ml HCl 37% and 35 ml water. The mixture was cooled to 5° C. and 0.8 g sodium nitrite dissolved in 5 ml water was added dropwise. The mixture was stirred for 30 minutes at 5° C. The crude product was filtered, washed with water and dried. Yield 80%. The product was crystallized from methanol. The structure was confirmed by IR and NMR spectroscopy.

후처리

  1. stirringThe mixture was stirred for 2 hours at 15° C
  2. washThe organic solution was washed with HCl 2N
  3. customdried
  4. customthe solvent was removed under vacuum
  5. customto obtain a yellow-red oil, that
  6. customAfter 15 minutes the crude product separated
  7. filtrationwas filtered under vacuum
  8. additionwas added dropwise
  9. stirringThe mixture was stirred for 30 minutes at 5° C
  10. filtrationThe crude product was filtered
  11. washwashed with water
  12. customdried
  13. customThe product was crystallized from methanol

출처 및 근거

ORD 기록
ord-6bb0f49f7b484b7d9fc48c25f6532664
출처 데이터셋
uspto-grants-1993_08
특허 번호
US05232826

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