Acetic Acid → Oxaprozin

HRID 1449341

반응식

HRID 1449341 반응식
C(O)(=O)C.[C:5]([OH:12])(=O)[CH2:6][CH2:7][C:8]([OH:10])=[O:9].[C:13]1([C:19]([CH:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)O)=O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C1(C(C(C2C=CC=CC=2)O)=O)C=CC=CC=1.C([O-])(=O)C.[NH4+:49]>O>[C:13]1([C:19]2[N:49]=[C:5]([CH2:6][CH2:7][C:8]([OH:10])=[O:9])[O:12][C:21]=2[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

참가 물질

5

반응물 3

HCID 176Acetic Acid2회HCID 517165Ammonium AcetateHCID 131711721Butanedioic acid;bis(2-hydroxy-1,2-diphenylethanone)

생성물 1

HCID 4614Oxaprozin

시약·촉매·용매 1

HCID 962Water용매2회

실험 절차

A clean dry reactor of 50 gallon capacity (227 liters) was charged with glacial acetic acid (92.0 kg.). With agitation benzoin hemisuccinate (25.3 kg.) prepared as described under part A and ammonium acetate (31 kg.) were added. The reaction mixture was heated to 90°-95° C. and stirred at this temperature range for 11/2 hours. Water (44.0 kg.) was carefully added to the reaction mixture and the mixture was reheated to 90°-95° C. The mixture was then transferred to another reactor of 50 gallon capacity (227 litres) through a pre-heated pressure filter. The first reactor and the filter were washed through with a mixture of glacial acetic acid (13.3 kg.) and water (6.2 kg.). The mixture in the reactor was then cooled to 10°-15° C. with agitation and the product was filtered on a ceramic filter. The product on the ceramic filter was then washed with a mixture prepared by adding glacial acetic acid (25.5 kg.) with agitation to water (12.5 kg.). The product on the filter was sucked well dry and then washed with demineralised water (10 kg.) and sucked well dry. The product was dried in a Mitchell oven at 80° C. for 16-18 hours. The yield of crude β-(4,5-diphenyloxazol-2-yl)propionic acid was 17.5 kg. (67% overall yield for parts A and B).

후처리

  1. additionwere added
  2. temperatureThe reaction mixture was heated to 90°-95° C.
  3. customwas reheated to 90°-95° C
  4. customThe mixture was then transferred to another reactor of 50 gallon capacity (227 litres) through a pre-heated pressure
  5. filtrationfilter
  6. washThe first reactor and the filter were washed through with a mixture of glacial acetic acid (13.3 kg.) and water (6.2 kg.)
  7. temperatureThe mixture in the reactor was then cooled to 10°-15° C. with agitation
  8. filtrationthe product was filtered on a ceramic filter
  9. filtrationThe product on the ceramic filter
  10. washwas then washed with a mixture
  11. customprepared
  12. customThe product on the filter was sucked well dry
  13. washwashed with demineralised water (10 kg.)
  14. customsucked well dry
  15. customThe product was dried in a Mitchell oven at 80° C. for 16-18 hours
  16. custom(67% overall yield for parts A and B)

출처 및 근거

ORD 기록
ord-157c2176d6a742bfb003f8239f529c94
출처 데이터셋
uspto-grants-1980_02
특허 번호
US04190584

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