Bromide ion → Pseudourea, 2-(p-nitrobenzyl)-2-thio-, monohydrobromide

HRID 1513325노트

반응식

HRID 1513325 반응식
[NH2:1][C:2]([NH2:4])=[S:3].[N+:5]([C:8]1[CH:13]=[CH:12][C:11]([CH2:14][Br:15])=[CH:10][CH:9]=1)([O-:7])=[O:6].[Br-]>CC(C)=O>[BrH:15].[N+:5]([C:8]1[CH:13]=[CH:12][C:11]([CH2:14][S:3][C:2](=[NH:4])[NH2:1])=[CH:10][CH:9]=1)([O-:7])=[O:6]

참가 물질

5

반응물 3

HCID 259Bromide ion2회HCID 660114-Nitrobenzyl bromideHCID 2723790Thiourea2회

생성물 1

HCID 116350Pseudourea, 2-(p-nitrobenzyl)-2-thio-, monohydrobromide수율 94.1%

시약·촉매·용매 1

HCID 180Acetone용매2회

실험 절차

Thiourea (8c) (1.55 kg) and acetone (30 L) were added to a 72-L reactor under a nitrogen atmosphere. The mixture was agitated. 4-nitrophenylmethyl bromide (8d) (4.00 kg) and acetone (15 L) were added to a separate flask. The mixture was stirred until the bromide dissolved (warming may be required). The solution of the bromide was added to the mixture of thiourea, keeping the temperature below 40° C. A thick solution formed within 30 minutes. After stiffing for 2 h, HPLC analysis of the mixture shows >99% conversion. The mixture was filtered, and the filter cake was rinsed with a 1:1 MTBE: acetone solution (8 L). The solids were dried to give 5.09 kg (93% yield) of the desired product (8a) as a white solid.

후처리

  1. dissolutiondissolved
  2. temperature(warming may be required)
  3. customthe temperature below 40° C
  4. customA thick solution formed within 30 minutes
  5. filtrationThe mixture was filtered
  6. washthe filter cake was rinsed with a 1:1 MTBE
  7. customThe solids were dried

출처 및 근거

ORD 기록
ord-a2ddd57e1f59443f9dfb1d9db5f8f946
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08217172B2

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