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Phosgene → 2-(Chloromethyl)-N-[(4,6-dimethoxypyrimidin-2-yl)-aminocarbonyl]benzenesulfonamide

HRID 4137
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HRID 4137 반응식
[Cl:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9]([NH:12][C:13]([NH:15][CH2:16]CCC)=[O:14])(=[O:11])=[O:10].C(Cl)(Cl)=O.ClCC1C=CC=CC=1S(N=C=O)(=O)=O.S(N=C=O)(N=C=O)(=O)=O.NC1[N:53]=[C:52]([O:54][CH3:55])[CH:51]=[C:50]([O:56][CH3:57])[N:49]=1>C1(C)C(C)=CC=CC=1.N12CCC(CC1)CN2.C(#N)C>[Cl:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9]([NH:12][C:13]([NH:15][C:16]1[N:53]=[C:52]([O:54][CH3:55])[CH:51]=[C:50]([O:56][CH3:57])[N:49]=1)=[O:14])(=[O:10])=[O:11]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

9

반응물 5

HCID 6371PhosgeneHCID 77898Sulphonyl diisocyanateHCID 1189462-Amino-4,6-dimethoxypyrimidineHCID 136318872-(Chloromethyl)-N-(butylaminocarbonyl)benzenesulfonamideHCID 201526992-(Chloromethyl)benzenesulfonyl isocyanate

생성물 1

HCID 133646172-(Chloromethyl)-N-[(4,6-dimethoxypyrimidin-2-yl)-aminocarbonyl]benzenesulfonamide
수율 69.6%

시약·촉매·용매 3

HCID 136165Diazabicyclo(2.2.2)octane촉매HCID 6342Acetonitrile용매HCID 7237O-Xylene용매

실험 절차

A solution of 2-(chloromethyl)-N-(butylaminocarbonyl)benzene sulfonamide (1.33 g, 4.38 mmol) and diazabicyclo[2.2.2]octane (5 mg) in xylene (12 ml) was heated at reflux and contacted in portions with phosgene (1.0 ml. condensed phase). After 2.0 hrs at reflux, the mixture was cooled to room temperature, decanted, and volatiles were removed to give 1.56 g of crude product. The IR spectrum of 2-(chloromethyl)benzenesulfonyl isocyanate featured a strong band at 2250 cm-1. The crude sulfonyl isocyanate was contacted with acetonitrile (10 ml) and 2-amino-4,6-dimethoxypyrimidine (0.68 g, 4.4 mmol) and stirred for 16 hrs. Filtration gave 1.18 g of white solid, mp 192°-193°. The sample was dissolved in 0.5N NaOH, filtered and pH adjusted to 6.5. The mixture was cooled and filtered and the solid washed with ice water and dried to give 0.90 g of white solid. 1H nmr δDMSO-d6TMS 12.7 (brd s, 10.50 (s, 1H) 8.13-7.97 (m, 1H), 7.73-7.40 (m, 3H), 5.90 (s, 1H), 5.10 (s, 2H), 3.87 (s, 6H).

후처리

  1. temperatureat reflux
  2. temperatureAfter 2.0 hrs at reflux
  3. customdecanted
  4. customvolatiles were removed
  5. customto give 1.56 g of crude product
  6. filtrationFiltration

출처 및 근거

ORD 기록
ord-7101f12d796b4a7697ca6546a96de61b
출처 데이터셋
uspto-grants-1988_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04723990

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