Water → 4-(Carbamoylamino)-4,5,6,7-tetrahydro-1-benzothiophen-7-yl benzoate

HRID 1973907Notes

Reaction equation

HRID 1973907 reaction equation
[OH:1][CH:2]1[C:7]2[S:8][CH:9]=[CH:10][C:6]=2[CH:5]([NH:11][C:12]([NH2:14])=[O:13])[CH2:4][CH2:3]1.[C:15](Cl)(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O>N1C=CC=CC=1>[C:15]([O:1][CH:2]1[C:7]2[S:8][CH:9]=[CH:10][C:6]=2[CH:5]([NH:11][C:12]([NH2:14])=[O:13])[CH2:4][CH2:3]1)(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7412Benzoyl chloride2×HCID 20348930N-(7-Hydroxy-4,5,6,7-tetrahydro-1-benzothiophen-4-yl)urea

Product 1

HCID 214909494-(Carbamoylamino)-4,5,6,7-tetrahydro-1-benzothiophen-7-yl benzoate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In 5 ml of pyridine, 0.53 g of 4,5,6,7-tetrahydro-7-hydroxybenzo[b]thien-4-ylurea is stirred and 0.39 g of benzoyl chloride added under a nitrogen atmosphere. The mixture is stirred at room temperature and after 1 hr, an additional 0.2 g of benzoyl chloride is added. After another 0.75 hr, the mixture is poured into H2O and the white precipitate is collected. The solid is washed with H2O, dried, dissolved in acetone-hexane and filtered to remove an insoluble material. The filtrate is evaporated to dryness and the acetone-hexane treatments are repeated twice to remove additional side product. The solid from the filtrate is recrystallized from ethyl acetate to give a solid with m.p. 199° C-205° C.

Workup

  1. waitAfter another 0.75 hr
  2. customthe white precipitate is collected
  3. washThe solid is washed with H2O
  4. customdried
  5. dissolutiondissolved in acetone-hexane
  6. filtrationfiltered
  7. customto remove an insoluble material
  8. customThe filtrate is evaporated to dryness
  9. customto remove additional side product
  10. customThe solid from the filtrate is recrystallized from ethyl acetate
  11. customto give a solid with m.p. 199° C-205° C.

Sources & evidence

ORD record
ord-6112f4502c9341b981370986d5a4561c
Source dataset
uspto-grants-1976_12
Patent number
US03998959

Reaction notes

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