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Ammonia → Methyl 4-methoxy-2-sulfamoylbenzoate

HRID 1249463
Notes
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Reaction equation

HRID 1249463 reaction equation
Cl[S:2]([C:5]1[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8])(=[O:4])=[O:3].[NH3:17].O>ClCCl>[NH2:17][S:2]([C:5]1[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8])(=[O:4])=[O:3]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 222AmmoniaHCID 962WaterHCID 13769571Methyl 2-(chlorosulfonyl)-4-methoxybenzoate

Product 1

HCID 13769572Methyl 4-methoxy-2-sulfamoylbenzoateYield 25.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-10 °C

Procedure

A solution of 554 g of the compound of Example 4 in 5 L of dichloromethane was cooled to -40° C. and 79 g of anhydrous ammonia was added at this temperature. The reaction mixture was allowed to warm to -10° C., stirred 1 hour, then poured into 6 L of water. The organic phase was separated and filtered. The filter cake was washed with dichloromethane and dried giving 356 g of crude product. A 180 g portion was recrystallized from methanol to give 130 g of the title compound, m.p. 139°-142° C.

Workup

  1. customThe organic phase was separated
  2. filtrationfiltered
  3. washThe filter cake was washed with dichloromethane
  4. customdried
  5. customgiving 356 g of crude product
  6. customA 180 g portion was recrystallized from methanol

Sources & evidence

ORD record
ord-cc175d25fd0140b590023b0642c12631
Source dataset
uspto-grants-1986_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04632693

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes