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

HRID 1153861

반응식

HRID 1153861 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 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]benzenesulfonamide수율 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-d1474643f54545e58f823dac03036fc3
출처 데이터셋
uspto-grants-1984_12
특허 번호
US04486589

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